Process for synthesis of N-(hydrocarbyl)substituted-p-menthane-3-carboxamide
This invention provides an improved process for synthesizing carboxamides which involves reacting 3-p-menthyl halide with magnesium to form 3-p-menthylmagnesium halide Grignard reagent, and reacting the Grignard reagent with hydrocarbyl isocyanate at a temperature below about -20 DEG C. to form N-hy...
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| creator | HAUT STEPHEN A COMES ROGER A |
| description | This invention provides an improved process for synthesizing carboxamides which involves reacting 3-p-menthyl halide with magnesium to form 3-p-menthylmagnesium halide Grignard reagent, and reacting the Grignard reagent with hydrocarbyl isocyanate at a temperature below about -20 DEG C. to form N-hydrocarbyl-p-menthane-3-carboxamide product. The product comprises a mixture of geometric isomers in which the 3-p-menthyl:3-p-neomenthyl weight ratio is at least 4:1 and can be as high as 9:1 under optimal conditions. This invention also provides a novel process for producing acylurea compounds such as N-(3-p-menthylcarbonyl)-N-t-butyl-N'-t-butylurea. |
| format | Patent |
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The product comprises a mixture of geometric isomers in which the 3-p-menthyl:3-p-neomenthyl weight ratio is at least 4:1 and can be as high as 9:1 under optimal conditions. This invention also provides a novel process for producing acylurea compounds such as N-(3-p-menthylcarbonyl)-N-t-butyl-N'-t-butylurea.</description><language>eng</language><subject>CHEMISTRY ; HETEROCYCLIC COMPOUNDS ; METALLURGY ; ORGANIC CHEMISTRY</subject><creationdate>1982</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=19821228&DB=EPODOC&CC=US&NR=4366317A$$EHTML$$P50$$Gepo$$Hfree_for_read</linktohtml><link.rule.ids>230,308,776,881,25542,76289</link.rule.ids><linktorsrc>$$Uhttps://worldwide.espacenet.com/publicationDetails/biblio?FT=D&date=19821228&DB=EPODOC&CC=US&NR=4366317A$$EView_record_in_European_Patent_Office$$FView_record_in_$$GEuropean_Patent_Office$$Hfree_for_read</linktorsrc></links><search><creatorcontrib>HAUT; STEPHEN A</creatorcontrib><creatorcontrib>COMES; ROGER A</creatorcontrib><title>Process for synthesis of N-(hydrocarbyl)substituted-p-menthane-3-carboxamide</title><description>This invention provides an improved process for synthesizing carboxamides which involves reacting 3-p-menthyl halide with magnesium to form 3-p-menthylmagnesium halide Grignard reagent, and reacting the Grignard reagent with hydrocarbyl isocyanate at a temperature below about -20 DEG C. to form N-hydrocarbyl-p-menthane-3-carboxamide product. The product comprises a mixture of geometric isomers in which the 3-p-menthyl:3-p-neomenthyl weight ratio is at least 4:1 and can be as high as 9:1 under optimal conditions. This invention also provides a novel process for producing acylurea compounds such as N-(3-p-menthylcarbonyl)-N-t-butyl-N'-t-butylurea.</description><subject>CHEMISTRY</subject><subject>HETEROCYCLIC COMPOUNDS</subject><subject>METALLURGY</subject><subject>ORGANIC CHEMISTRY</subject><fulltext>true</fulltext><rsrctype>patent</rsrctype><creationdate>1982</creationdate><recordtype>patent</recordtype><sourceid>EVB</sourceid><recordid>eNrjZPAJKMpPTi0uVkjLL1IorswryUgtzixWyE9T8NPVyKhMAcomFiVV5mgWlyYVl2SWlJakpugW6OamAlUm5qXqGuuC5PMrEnMzU1J5GFjTEnOKU3mhNDeDvJtriLOHbmpBfnxqcUFicmpeakl8aLCJsZmZsaG5ozFhFQDgJzVT</recordid><startdate>19821228</startdate><enddate>19821228</enddate><creator>HAUT; STEPHEN A</creator><creator>COMES; ROGER A</creator><scope>EVB</scope></search><sort><creationdate>19821228</creationdate><title>Process for synthesis of N-(hydrocarbyl)substituted-p-menthane-3-carboxamide</title><author>HAUT; STEPHEN A ; COMES; ROGER A</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-epo_espacenet_US4366317A3</frbrgroupid><rsrctype>patents</rsrctype><prefilter>patents</prefilter><language>eng</language><creationdate>1982</creationdate><topic>CHEMISTRY</topic><topic>HETEROCYCLIC COMPOUNDS</topic><topic>METALLURGY</topic><topic>ORGANIC CHEMISTRY</topic><toplevel>online_resources</toplevel><creatorcontrib>HAUT; STEPHEN A</creatorcontrib><creatorcontrib>COMES; ROGER A</creatorcontrib><collection>esp@cenet</collection></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext_linktorsrc</fulltext></delivery><addata><au>HAUT; STEPHEN A</au><au>COMES; ROGER A</au><format>patent</format><genre>patent</genre><ristype>GEN</ristype><title>Process for synthesis of N-(hydrocarbyl)substituted-p-menthane-3-carboxamide</title><date>1982-12-28</date><risdate>1982</risdate><abstract>This invention provides an improved process for synthesizing carboxamides which involves reacting 3-p-menthyl halide with magnesium to form 3-p-menthylmagnesium halide Grignard reagent, and reacting the Grignard reagent with hydrocarbyl isocyanate at a temperature below about -20 DEG C. to form N-hydrocarbyl-p-menthane-3-carboxamide product. The product comprises a mixture of geometric isomers in which the 3-p-menthyl:3-p-neomenthyl weight ratio is at least 4:1 and can be as high as 9:1 under optimal conditions. This invention also provides a novel process for producing acylurea compounds such as N-(3-p-menthylcarbonyl)-N-t-butyl-N'-t-butylurea.</abstract><oa>free_for_read</oa></addata></record> |
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| title | Process for synthesis of N-(hydrocarbyl)substituted-p-menthane-3-carboxamide |
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