Process of preparing beta-substituted polymethine dyestuffs
2-(2 - Methylmercapto - 3 - p - dimethylaminobenzalpropenyl)-benzthiazole ethiodide is prepared by boiling together 2-(2-methylmercaptopropenyl)-benzthiazole ethyl methosulphate, p-dimethylaminobenzaldehyde and acetic anhydride, and treating the product with aqueous potassium iodide solution. 1 - Ph...
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| description | 2-(2 - Methylmercapto - 3 - p - dimethylaminobenzalpropenyl)-benzthiazole ethiodide is prepared by boiling together 2-(2-methylmercaptopropenyl)-benzthiazole ethyl methosulphate, p-dimethylaminobenzaldehyde and acetic anhydride, and treating the product with aqueous potassium iodide solution. 1 - Phenyl - 3 - methyl - 4 - (31 - ethyldihydrobenzthiazolylidene - g - methylmercaptobutenylidene)-5-pyrazolone is prepared by reacting together 2 - (2 - methylmercaptopropenyl) - benzthiazole ethyl methosulphate, 4-anilidomethylene - 1 - phenyl - 3 - methyl - 5 - pyrazolone, acetic anhydride, and sodium acetate. 2 - (2 - Phenylmercaptopropenyl) - benzthiazole ethochloride is prepared by reacting 2-(2-chloropropenyl) - benzthiazole ethochloride with sodium thiophenolate. 2 - (2 - Methoxypropenyl) - benzthiazole ethiodide is prepared by reacting 2-acetylmethylene-N-ethylbenzthiazoline with methyl iodide. Samples have been furnished under Sect. 2 (5) of five dyes, the preparation of the intermediates for which is as follows. 2-(b -ethoxy: b - methylvinyl) - benzoelenazole methyl ethyl sulphate is prepared by refluxing 2-acetylmethylene - N - methyldihydrobenzselenazole with diethyl sulphate and benzene, 2-(b -ethoxy: b -methylvinyl)-6-methylbenzthiazole methyl ethyl sulphate, 2-(b -ethoxy: b -methylvinyl)-benzthiazole benzyl ethylsulphate, and 2-(b -methoxy: b -methylvinyl) - 3 : 4 - (a - methyltrimethylene) - benzthiazole dimethylsulphate are similarly prepared. N - Acetyl - 2 - methyl - 1 : 2 : 3 : 4 - tetrahydroquinoline is prepared by boiling 2-methyl-1 : 2 : 3 : 4-tetrahydroquinoline with acetic acid and acetic anhydride. N-Thioacetyl-2-methyl-1 : 2 : 3 : 4-tetrahydroquinoline is prepared by refluxing the N-acetyl compound with P2S5 in toluene. 2 - Methyl - 3 : 4 - a - methyltrimethylenebenzthiazole bromide is prepared by reacting the N-thioacetyl compound with bromine in chloroform. 2 - Acetyl - methylene - 3 : 4 - a - methyltrimethylenedihydrobenzthiazole is prepared by reacting 2-methyl-3 : 4-a -methyltrimethylenebenzthiazole bromide in pyridine with acetaldehyde. 2-(b -Chloro-b -methylvinyl)-benzthiazole ethochloride is prepared by reacting 2-acetylmethylene - N - ethyl - 2 : 3 - dihydrobenzthiazole in benzene with POCl3. 2-(b -Benzthiazolylmercapto: b - methylvinyl) - benzthiazole ethochloride is prepared by adding the b -chloro compound to a warm solution of the potassium salt of 2-mercaptobenzthiazole in pyridine. Specification 623,990 is referred to.ALSO: |
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| fullrecord | <record><control><sourceid>epo_EVB</sourceid><recordid>TN_cdi_epo_espacenet_US2557806A</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>US2557806A</sourcerecordid><originalsourceid>FETCH-epo_espacenet_US2557806A3</originalsourceid><addsrcrecordid>eNrjZLAOKMpPTi0uVshPUygoSi1ILMrMS1dISi1J1C0uTSouySwpLUlNUSjIz6nMTS3JyMxLVUipTC0uKU1LK-ZhYE1LzClO5YXS3Azybq4hzh66qQX58anFBYnJqXmpJfGhwUampuYWBmaOxoRVAABbLC--</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>patent</recordtype></control><display><type>patent</type><title>Process of preparing beta-substituted polymethine dyestuffs</title><source>esp@cenet</source><creator>STRAETE LEO ARNOLD VAN DE ; SCHOUWENAARS MARCEL ADAM</creator><creatorcontrib>STRAETE LEO ARNOLD VAN DE ; SCHOUWENAARS MARCEL ADAM</creatorcontrib><description>2-(2 - Methylmercapto - 3 - p - dimethylaminobenzalpropenyl)-benzthiazole ethiodide is prepared by boiling together 2-(2-methylmercaptopropenyl)-benzthiazole ethyl methosulphate, p-dimethylaminobenzaldehyde and acetic anhydride, and treating the product with aqueous potassium iodide solution. 1 - Phenyl - 3 - methyl - 4 - (31 - ethyldihydrobenzthiazolylidene - g - methylmercaptobutenylidene)-5-pyrazolone is prepared by reacting together 2 - (2 - methylmercaptopropenyl) - benzthiazole ethyl methosulphate, 4-anilidomethylene - 1 - phenyl - 3 - methyl - 5 - pyrazolone, acetic anhydride, and sodium acetate. 2 - (2 - Phenylmercaptopropenyl) - benzthiazole ethochloride is prepared by reacting 2-(2-chloropropenyl) - benzthiazole ethochloride with sodium thiophenolate. 2 - (2 - Methoxypropenyl) - benzthiazole ethiodide is prepared by reacting 2-acetylmethylene-N-ethylbenzthiazoline with methyl iodide. Samples have been furnished under Sect. 2 (5) of five dyes, the preparation of the intermediates for which is as follows. 2-(b -ethoxy: b - methylvinyl) - benzoelenazole methyl ethyl sulphate is prepared by refluxing 2-acetylmethylene - N - methyldihydrobenzselenazole with diethyl sulphate and benzene, 2-(b -ethoxy: b -methylvinyl)-6-methylbenzthiazole methyl ethyl sulphate, 2-(b -ethoxy: b -methylvinyl)-benzthiazole benzyl ethylsulphate, and 2-(b -methoxy: b -methylvinyl) - 3 : 4 - (a - methyltrimethylene) - benzthiazole dimethylsulphate are similarly prepared. N - Acetyl - 2 - methyl - 1 : 2 : 3 : 4 - tetrahydroquinoline is prepared by boiling 2-methyl-1 : 2 : 3 : 4-tetrahydroquinoline with acetic acid and acetic anhydride. N-Thioacetyl-2-methyl-1 : 2 : 3 : 4-tetrahydroquinoline is prepared by refluxing the N-acetyl compound with P2S5 in toluene. 2 - Methyl - 3 : 4 - a - methyltrimethylenebenzthiazole bromide is prepared by reacting the N-thioacetyl compound with bromine in chloroform. 2 - Acetyl - methylene - 3 : 4 - a - methyltrimethylenedihydrobenzthiazole is prepared by reacting 2-methyl-3 : 4-a -methyltrimethylenebenzthiazole bromide in pyridine with acetaldehyde. 2-(b -Chloro-b -methylvinyl)-benzthiazole ethochloride is prepared by reacting 2-acetylmethylene - N - ethyl - 2 : 3 - dihydrobenzthiazole in benzene with POCl3. 2-(b -Benzthiazolylmercapto: b - methylvinyl) - benzthiazole ethochloride is prepared by adding the b -chloro compound to a warm solution of the potassium salt of 2-mercaptobenzthiazole in pyridine. Specification 623,990 is referred to.ALSO:Symmetrical and unsymmetrical polymethine dyes are prepared by reacting a compound of the general formula <FORM:0633824/IV (c)/1> wherein R1 is S-alkyl, S-aryl, S-substituted alkyl, Se-alkyl, Se-substituted alkyl, O-alkyl, O-substituted alkyl, or S-Q, wherein Q represents a heterocyclic nucleus (e.g. benzthiazole), Y represents the atom grouping necessary to complete a heterocyclic 5-membered ring which may have a fused-on aromatic ring, R is alkyl, aralkyl, aryl, carboxyalkyl, or a substituted or unsubstituted trimethylene bridge between the N-atom and the peri-C-atom, and X is an acid residue, either with an aromatic aldehyde, or with a compound of one of the formul <FORM:0633824/IV (c)/2> and <FORM:0633824/IV (c)/3> wherein R3 is a group reacting with the CH3 group, Z is the non-metallic atoms to complete a 5- or 6-membered heterocyclic ring (which may have a fused-on aromatic ring, n is O or a positive integer, and R4 and X are as R and X above. Compounds of the general formula specified are 2-(2-methylmercaptopropenyl) - benzthiazole ethyl methosulphate, 2 - (2 - methylmercaptopropenyl) - 4 : 5 - naphthathiazole ethyl methosulphate, 2-(2-methylmercaptopropenyl) - 3 : 4 - trimethylene benzthiazole methosulphate, 2 - benzylmercaptopropenyl) - benzthiazole ethobromide, 2 - (b -carboxyethylmercaptopropenyl) - benzthiazole ethochloride, 2 - (2 - methylselenamercaptopropenyl) - benzthiazole ethyl methosulphate, 2 - (2 - methoxypropenyl) - benzthiazole ethiodide, and 2-(2-phenylmercaptopropenyl)-benzthiazole ethochloride. 3 : 31 - Diethyl - 9 - methylmercaptothiacarbocyanine perchlorate is prepared by boiling together 2 - (2 - methylmercaptopropenyl)-benzthiazole ethyl methosulphate, 2-methyl-mercaptobenzthiazole ethyl p-toluenesulphonate, pyridine, and triethylamine, and treating the product with aqueous sodium perchlorate. 3 : 31 - diethyl - 9 - methylmercapto - 4 : 5-benzthiacarbocyanine perchlorate, 3 - ethyl-31 : 41 - trimethylene - 9 - methylmercaptothiacarbocyanine perchlorate, 3 : 31 - diethyl-9 - methylmercaptothiaquinocarbocyanine perchlorate, 3 : 31 - diethyl - 9 - benzylmercaptothiacarbocyanine perchlorate, 3 : 31 - diethyl-9 - b - carboxyethylmercaptothiacarbocyanine perchlorate, 3 : 31 - diethyl - 9 - phenylmercaptothiacarbocyanine chloride, 3 : 31 - diethyl - 9-methylselenamercaptothiacarbocyanine iodide, 3 : 31 - diethyl - 9 - methoxythiacarbocyanine perchlorate, and 3 - ethyl - 31 - methyl - 51-methylmercapto - 9 - methoxythiathiadiazolocarbocyanine perchlorate are similarly prepared. 3 - Ethyl - 31 - methyl - 9 - methylmercaptothiadicarbocyanine iodide is prepared by reacting together 2-b -acetanilidovinyl-benzthiazole methyl methosulphate and 2-(2-methylmercaptopropenyl)-benzthiazole ethyl methosulphate in the presence of acetic anhydride and sodium acetate, and treating the product with aqueous potassium iodide solution. Samples have been furnished under Sect. 2(5) of 3 : 31 - dimethyl - 9 - ethoxy - thiaselenacarbocyanine perchlorate, of 3 : 31 : 61-trimethyl - 5 - methylmercapto - 9 - ethoxythiadiazolo - (1 : 3 : 4) - thiacarbocyanineiodide, of 3 p - methyl - 31 - benzyl - 9 - ethoxy oxathiacarbocyanine methylsulphate, of 3-ethyl - 31 : 41 - (a - methyltrimethylene) - 9-methoxythiacarbocyanine perchlorate, and of 3 - methyl - 31 - ethyl - 9 - benzthiazolyl - (2)-mercaptothiacarbocyanine perchlorate. Specification 623,990 is referred to.</description><language>eng</language><subject>ADHESIVES ; CHEMISTRY ; DYES ; LAKES ; METALLURGY ; MISCELLANEOUS APPLICATIONS OF MATERIALS ; MISCELLANEOUS COMPOSITIONS ; MORDANTS ; NATURAL RESINS ; ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES ; PAINTS ; POLISHES</subject><creationdate>1951</creationdate><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://worldwide.espacenet.com/publicationDetails/biblio?FT=D&date=19510619&DB=EPODOC&CC=US&NR=2557806A$$EHTML$$P50$$Gepo$$Hfree_for_read</linktohtml><link.rule.ids>230,308,776,881,25542,76289</link.rule.ids><linktorsrc>$$Uhttps://worldwide.espacenet.com/publicationDetails/biblio?FT=D&date=19510619&DB=EPODOC&CC=US&NR=2557806A$$EView_record_in_European_Patent_Office$$FView_record_in_$$GEuropean_Patent_Office$$Hfree_for_read</linktorsrc></links><search><creatorcontrib>STRAETE LEO ARNOLD VAN DE</creatorcontrib><creatorcontrib>SCHOUWENAARS MARCEL ADAM</creatorcontrib><title>Process of preparing beta-substituted polymethine dyestuffs</title><description>2-(2 - Methylmercapto - 3 - p - dimethylaminobenzalpropenyl)-benzthiazole ethiodide is prepared by boiling together 2-(2-methylmercaptopropenyl)-benzthiazole ethyl methosulphate, p-dimethylaminobenzaldehyde and acetic anhydride, and treating the product with aqueous potassium iodide solution. 1 - Phenyl - 3 - methyl - 4 - (31 - ethyldihydrobenzthiazolylidene - g - methylmercaptobutenylidene)-5-pyrazolone is prepared by reacting together 2 - (2 - methylmercaptopropenyl) - benzthiazole ethyl methosulphate, 4-anilidomethylene - 1 - phenyl - 3 - methyl - 5 - pyrazolone, acetic anhydride, and sodium acetate. 2 - (2 - Phenylmercaptopropenyl) - benzthiazole ethochloride is prepared by reacting 2-(2-chloropropenyl) - benzthiazole ethochloride with sodium thiophenolate. 2 - (2 - Methoxypropenyl) - benzthiazole ethiodide is prepared by reacting 2-acetylmethylene-N-ethylbenzthiazoline with methyl iodide. Samples have been furnished under Sect. 2 (5) of five dyes, the preparation of the intermediates for which is as follows. 2-(b -ethoxy: b - methylvinyl) - benzoelenazole methyl ethyl sulphate is prepared by refluxing 2-acetylmethylene - N - methyldihydrobenzselenazole with diethyl sulphate and benzene, 2-(b -ethoxy: b -methylvinyl)-6-methylbenzthiazole methyl ethyl sulphate, 2-(b -ethoxy: b -methylvinyl)-benzthiazole benzyl ethylsulphate, and 2-(b -methoxy: b -methylvinyl) - 3 : 4 - (a - methyltrimethylene) - benzthiazole dimethylsulphate are similarly prepared. N - Acetyl - 2 - methyl - 1 : 2 : 3 : 4 - tetrahydroquinoline is prepared by boiling 2-methyl-1 : 2 : 3 : 4-tetrahydroquinoline with acetic acid and acetic anhydride. N-Thioacetyl-2-methyl-1 : 2 : 3 : 4-tetrahydroquinoline is prepared by refluxing the N-acetyl compound with P2S5 in toluene. 2 - Methyl - 3 : 4 - a - methyltrimethylenebenzthiazole bromide is prepared by reacting the N-thioacetyl compound with bromine in chloroform. 2 - Acetyl - methylene - 3 : 4 - a - methyltrimethylenedihydrobenzthiazole is prepared by reacting 2-methyl-3 : 4-a -methyltrimethylenebenzthiazole bromide in pyridine with acetaldehyde. 2-(b -Chloro-b -methylvinyl)-benzthiazole ethochloride is prepared by reacting 2-acetylmethylene - N - ethyl - 2 : 3 - dihydrobenzthiazole in benzene with POCl3. 2-(b -Benzthiazolylmercapto: b - methylvinyl) - benzthiazole ethochloride is prepared by adding the b -chloro compound to a warm solution of the potassium salt of 2-mercaptobenzthiazole in pyridine. Specification 623,990 is referred to.ALSO:Symmetrical and unsymmetrical polymethine dyes are prepared by reacting a compound of the general formula <FORM:0633824/IV (c)/1> wherein R1 is S-alkyl, S-aryl, S-substituted alkyl, Se-alkyl, Se-substituted alkyl, O-alkyl, O-substituted alkyl, or S-Q, wherein Q represents a heterocyclic nucleus (e.g. benzthiazole), Y represents the atom grouping necessary to complete a heterocyclic 5-membered ring which may have a fused-on aromatic ring, R is alkyl, aralkyl, aryl, carboxyalkyl, or a substituted or unsubstituted trimethylene bridge between the N-atom and the peri-C-atom, and X is an acid residue, either with an aromatic aldehyde, or with a compound of one of the formul <FORM:0633824/IV (c)/2> and <FORM:0633824/IV (c)/3> wherein R3 is a group reacting with the CH3 group, Z is the non-metallic atoms to complete a 5- or 6-membered heterocyclic ring (which may have a fused-on aromatic ring, n is O or a positive integer, and R4 and X are as R and X above. Compounds of the general formula specified are 2-(2-methylmercaptopropenyl) - benzthiazole ethyl methosulphate, 2 - (2 - methylmercaptopropenyl) - 4 : 5 - naphthathiazole ethyl methosulphate, 2-(2-methylmercaptopropenyl) - 3 : 4 - trimethylene benzthiazole methosulphate, 2 - benzylmercaptopropenyl) - benzthiazole ethobromide, 2 - (b -carboxyethylmercaptopropenyl) - benzthiazole ethochloride, 2 - (2 - methylselenamercaptopropenyl) - benzthiazole ethyl methosulphate, 2 - (2 - methoxypropenyl) - benzthiazole ethiodide, and 2-(2-phenylmercaptopropenyl)-benzthiazole ethochloride. 3 : 31 - Diethyl - 9 - methylmercaptothiacarbocyanine perchlorate is prepared by boiling together 2 - (2 - methylmercaptopropenyl)-benzthiazole ethyl methosulphate, 2-methyl-mercaptobenzthiazole ethyl p-toluenesulphonate, pyridine, and triethylamine, and treating the product with aqueous sodium perchlorate. 3 : 31 - diethyl - 9 - methylmercapto - 4 : 5-benzthiacarbocyanine perchlorate, 3 - ethyl-31 : 41 - trimethylene - 9 - methylmercaptothiacarbocyanine perchlorate, 3 : 31 - diethyl-9 - methylmercaptothiaquinocarbocyanine perchlorate, 3 : 31 - diethyl - 9 - benzylmercaptothiacarbocyanine perchlorate, 3 : 31 - diethyl-9 - b - carboxyethylmercaptothiacarbocyanine perchlorate, 3 : 31 - diethyl - 9 - phenylmercaptothiacarbocyanine chloride, 3 : 31 - diethyl - 9-methylselenamercaptothiacarbocyanine iodide, 3 : 31 - diethyl - 9 - methoxythiacarbocyanine perchlorate, and 3 - ethyl - 31 - methyl - 51-methylmercapto - 9 - methoxythiathiadiazolocarbocyanine perchlorate are similarly prepared. 3 - Ethyl - 31 - methyl - 9 - methylmercaptothiadicarbocyanine iodide is prepared by reacting together 2-b -acetanilidovinyl-benzthiazole methyl methosulphate and 2-(2-methylmercaptopropenyl)-benzthiazole ethyl methosulphate in the presence of acetic anhydride and sodium acetate, and treating the product with aqueous potassium iodide solution. Samples have been furnished under Sect. 2(5) of 3 : 31 - dimethyl - 9 - ethoxy - thiaselenacarbocyanine perchlorate, of 3 : 31 : 61-trimethyl - 5 - methylmercapto - 9 - ethoxythiadiazolo - (1 : 3 : 4) - thiacarbocyanineiodide, of 3 p - methyl - 31 - benzyl - 9 - ethoxy oxathiacarbocyanine methylsulphate, of 3-ethyl - 31 : 41 - (a - methyltrimethylene) - 9-methoxythiacarbocyanine perchlorate, and of 3 - methyl - 31 - ethyl - 9 - benzthiazolyl - (2)-mercaptothiacarbocyanine perchlorate. Specification 623,990 is referred to.</description><subject>ADHESIVES</subject><subject>CHEMISTRY</subject><subject>DYES</subject><subject>LAKES</subject><subject>METALLURGY</subject><subject>MISCELLANEOUS APPLICATIONS OF MATERIALS</subject><subject>MISCELLANEOUS COMPOSITIONS</subject><subject>MORDANTS</subject><subject>NATURAL RESINS</subject><subject>ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES</subject><subject>PAINTS</subject><subject>POLISHES</subject><fulltext>true</fulltext><rsrctype>patent</rsrctype><creationdate>1951</creationdate><recordtype>patent</recordtype><sourceid>EVB</sourceid><recordid>eNrjZLAOKMpPTi0uVshPUygoSi1ILMrMS1dISi1J1C0uTSouySwpLUlNUSjIz6nMTS3JyMxLVUipTC0uKU1LK-ZhYE1LzClO5YXS3Azybq4hzh66qQX58anFBYnJqXmpJfGhwUampuYWBmaOxoRVAABbLC--</recordid><startdate>19510619</startdate><enddate>19510619</enddate><creator>STRAETE LEO ARNOLD VAN DE</creator><creator>SCHOUWENAARS MARCEL ADAM</creator><scope>EVB</scope></search><sort><creationdate>19510619</creationdate><title>Process of preparing beta-substituted polymethine dyestuffs</title><author>STRAETE LEO ARNOLD VAN DE ; SCHOUWENAARS MARCEL ADAM</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-epo_espacenet_US2557806A3</frbrgroupid><rsrctype>patents</rsrctype><prefilter>patents</prefilter><language>eng</language><creationdate>1951</creationdate><topic>ADHESIVES</topic><topic>CHEMISTRY</topic><topic>DYES</topic><topic>LAKES</topic><topic>METALLURGY</topic><topic>MISCELLANEOUS APPLICATIONS OF MATERIALS</topic><topic>MISCELLANEOUS COMPOSITIONS</topic><topic>MORDANTS</topic><topic>NATURAL RESINS</topic><topic>ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES</topic><topic>PAINTS</topic><topic>POLISHES</topic><toplevel>online_resources</toplevel><creatorcontrib>STRAETE LEO ARNOLD VAN DE</creatorcontrib><creatorcontrib>SCHOUWENAARS MARCEL ADAM</creatorcontrib><collection>esp@cenet</collection></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext_linktorsrc</fulltext></delivery><addata><au>STRAETE LEO ARNOLD VAN DE</au><au>SCHOUWENAARS MARCEL ADAM</au><format>patent</format><genre>patent</genre><ristype>GEN</ristype><title>Process of preparing beta-substituted polymethine dyestuffs</title><date>1951-06-19</date><risdate>1951</risdate><abstract>2-(2 - Methylmercapto - 3 - p - dimethylaminobenzalpropenyl)-benzthiazole ethiodide is prepared by boiling together 2-(2-methylmercaptopropenyl)-benzthiazole ethyl methosulphate, p-dimethylaminobenzaldehyde and acetic anhydride, and treating the product with aqueous potassium iodide solution. 1 - Phenyl - 3 - methyl - 4 - (31 - ethyldihydrobenzthiazolylidene - g - methylmercaptobutenylidene)-5-pyrazolone is prepared by reacting together 2 - (2 - methylmercaptopropenyl) - benzthiazole ethyl methosulphate, 4-anilidomethylene - 1 - phenyl - 3 - methyl - 5 - pyrazolone, acetic anhydride, and sodium acetate. 2 - (2 - Phenylmercaptopropenyl) - benzthiazole ethochloride is prepared by reacting 2-(2-chloropropenyl) - benzthiazole ethochloride with sodium thiophenolate. 2 - (2 - Methoxypropenyl) - benzthiazole ethiodide is prepared by reacting 2-acetylmethylene-N-ethylbenzthiazoline with methyl iodide. Samples have been furnished under Sect. 2 (5) of five dyes, the preparation of the intermediates for which is as follows. 2-(b -ethoxy: b - methylvinyl) - benzoelenazole methyl ethyl sulphate is prepared by refluxing 2-acetylmethylene - N - methyldihydrobenzselenazole with diethyl sulphate and benzene, 2-(b -ethoxy: b -methylvinyl)-6-methylbenzthiazole methyl ethyl sulphate, 2-(b -ethoxy: b -methylvinyl)-benzthiazole benzyl ethylsulphate, and 2-(b -methoxy: b -methylvinyl) - 3 : 4 - (a - methyltrimethylene) - benzthiazole dimethylsulphate are similarly prepared. N - Acetyl - 2 - methyl - 1 : 2 : 3 : 4 - tetrahydroquinoline is prepared by boiling 2-methyl-1 : 2 : 3 : 4-tetrahydroquinoline with acetic acid and acetic anhydride. N-Thioacetyl-2-methyl-1 : 2 : 3 : 4-tetrahydroquinoline is prepared by refluxing the N-acetyl compound with P2S5 in toluene. 2 - Methyl - 3 : 4 - a - methyltrimethylenebenzthiazole bromide is prepared by reacting the N-thioacetyl compound with bromine in chloroform. 2 - Acetyl - methylene - 3 : 4 - a - methyltrimethylenedihydrobenzthiazole is prepared by reacting 2-methyl-3 : 4-a -methyltrimethylenebenzthiazole bromide in pyridine with acetaldehyde. 2-(b -Chloro-b -methylvinyl)-benzthiazole ethochloride is prepared by reacting 2-acetylmethylene - N - ethyl - 2 : 3 - dihydrobenzthiazole in benzene with POCl3. 2-(b -Benzthiazolylmercapto: b - methylvinyl) - benzthiazole ethochloride is prepared by adding the b -chloro compound to a warm solution of the potassium salt of 2-mercaptobenzthiazole in pyridine. Specification 623,990 is referred to.ALSO:Symmetrical and unsymmetrical polymethine dyes are prepared by reacting a compound of the general formula <FORM:0633824/IV (c)/1> wherein R1 is S-alkyl, S-aryl, S-substituted alkyl, Se-alkyl, Se-substituted alkyl, O-alkyl, O-substituted alkyl, or S-Q, wherein Q represents a heterocyclic nucleus (e.g. benzthiazole), Y represents the atom grouping necessary to complete a heterocyclic 5-membered ring which may have a fused-on aromatic ring, R is alkyl, aralkyl, aryl, carboxyalkyl, or a substituted or unsubstituted trimethylene bridge between the N-atom and the peri-C-atom, and X is an acid residue, either with an aromatic aldehyde, or with a compound of one of the formul <FORM:0633824/IV (c)/2> and <FORM:0633824/IV (c)/3> wherein R3 is a group reacting with the CH3 group, Z is the non-metallic atoms to complete a 5- or 6-membered heterocyclic ring (which may have a fused-on aromatic ring, n is O or a positive integer, and R4 and X are as R and X above. Compounds of the general formula specified are 2-(2-methylmercaptopropenyl) - benzthiazole ethyl methosulphate, 2 - (2 - methylmercaptopropenyl) - 4 : 5 - naphthathiazole ethyl methosulphate, 2-(2-methylmercaptopropenyl) - 3 : 4 - trimethylene benzthiazole methosulphate, 2 - benzylmercaptopropenyl) - benzthiazole ethobromide, 2 - (b -carboxyethylmercaptopropenyl) - benzthiazole ethochloride, 2 - (2 - methylselenamercaptopropenyl) - benzthiazole ethyl methosulphate, 2 - (2 - methoxypropenyl) - benzthiazole ethiodide, and 2-(2-phenylmercaptopropenyl)-benzthiazole ethochloride. 3 : 31 - Diethyl - 9 - methylmercaptothiacarbocyanine perchlorate is prepared by boiling together 2 - (2 - methylmercaptopropenyl)-benzthiazole ethyl methosulphate, 2-methyl-mercaptobenzthiazole ethyl p-toluenesulphonate, pyridine, and triethylamine, and treating the product with aqueous sodium perchlorate. 3 : 31 - diethyl - 9 - methylmercapto - 4 : 5-benzthiacarbocyanine perchlorate, 3 - ethyl-31 : 41 - trimethylene - 9 - methylmercaptothiacarbocyanine perchlorate, 3 : 31 - diethyl-9 - methylmercaptothiaquinocarbocyanine perchlorate, 3 : 31 - diethyl - 9 - benzylmercaptothiacarbocyanine perchlorate, 3 : 31 - diethyl-9 - b - carboxyethylmercaptothiacarbocyanine perchlorate, 3 : 31 - diethyl - 9 - phenylmercaptothiacarbocyanine chloride, 3 : 31 - diethyl - 9-methylselenamercaptothiacarbocyanine iodide, 3 : 31 - diethyl - 9 - methoxythiacarbocyanine perchlorate, and 3 - ethyl - 31 - methyl - 51-methylmercapto - 9 - methoxythiathiadiazolocarbocyanine perchlorate are similarly prepared. 3 - Ethyl - 31 - methyl - 9 - methylmercaptothiadicarbocyanine iodide is prepared by reacting together 2-b -acetanilidovinyl-benzthiazole methyl methosulphate and 2-(2-methylmercaptopropenyl)-benzthiazole ethyl methosulphate in the presence of acetic anhydride and sodium acetate, and treating the product with aqueous potassium iodide solution. Samples have been furnished under Sect. 2(5) of 3 : 31 - dimethyl - 9 - ethoxy - thiaselenacarbocyanine perchlorate, of 3 : 31 : 61-trimethyl - 5 - methylmercapto - 9 - ethoxythiadiazolo - (1 : 3 : 4) - thiacarbocyanineiodide, of 3 p - methyl - 31 - benzyl - 9 - ethoxy oxathiacarbocyanine methylsulphate, of 3-ethyl - 31 : 41 - (a - methyltrimethylene) - 9-methoxythiacarbocyanine perchlorate, and of 3 - methyl - 31 - ethyl - 9 - benzthiazolyl - (2)-mercaptothiacarbocyanine perchlorate. Specification 623,990 is referred to.</abstract><oa>free_for_read</oa></addata></record> |
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| recordid | cdi_epo_espacenet_US2557806A |
| source | esp@cenet |
| subjects | ADHESIVES CHEMISTRY DYES LAKES METALLURGY MISCELLANEOUS APPLICATIONS OF MATERIALS MISCELLANEOUS COMPOSITIONS MORDANTS NATURAL RESINS ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES PAINTS POLISHES |
| title | Process of preparing beta-substituted polymethine dyestuffs |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-05T14%3A49%3A07IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-epo_EVB&rft_val_fmt=info:ofi/fmt:kev:mtx:patent&rft.genre=patent&rft.au=STRAETE%20LEO%20ARNOLD%20VAN%20DE&rft.date=1951-06-19&rft_id=info:doi/&rft_dat=%3Cepo_EVB%3EUS2557806A%3C/epo_EVB%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true |