Selective one-pot synthesis of aminopolyhalobenzonitriles from polyhalobenzotrichlorides in anhydrous ammonia
[Display omitted] •Polyhalogenbenzotrichlorides react with NH3 to form aminopolyhalogenbenzonitriles.•One-pot ammonolysis+aminodefluorination occur in the range from −33 to 5°C.•Temperature of introducing the second amino group is higher by 60–100°C.•Efficient method to prepare high-purity mono- and...
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| Veröffentlicht in: | Journal of fluorine chemistry 2017-08, Vol.200, p.84-90 |
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| creator | Vaganova, Tamara A. Rodionov, Vladimir I. Chuikov, Igor P. Chochrina, Ekaterina A. Malykhin, Evgenij V. |
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•Polyhalogenbenzotrichlorides react with NH3 to form aminopolyhalogenbenzonitriles.•One-pot ammonolysis+aminodefluorination occur in the range from −33 to 5°C.•Temperature of introducing the second amino group is higher by 60–100°C.•Efficient method to prepare high-purity mono- and diaminobenzonitriles was developed.
Polyhalogenated benzotrichlorides (pentafluoro-, chlorotetrafluoro-, chlorotrifluoro-, and tetrafluorobenzotrichlorides) undergo one-pot ammonolysis+aminodefluorination by the action of anhydrous ammonia to form mono- and diamino derivatives of polyhalobenzonitriles. For the substrates comprising halogen at the para-position, the ammonolysis of the CCl3 group and the first aminodefluorination occur simultaneously in the temperature range from −33 to 5°C. The temperature of introducing the second NH2 group is higher by 60–100°C, whereby conditions were found for the selective synthesis of mono- and diaminopolyhalobenzonitriles. The use of anhydrous ammonia as a reagent and a solvent minimizes side reactions and simplifies an isolation of the high purity products. |
| doi_str_mv | 10.1016/j.jfluchem.2017.06.005 |
| format | Article |
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•Polyhalogenbenzotrichlorides react with NH3 to form aminopolyhalogenbenzonitriles.•One-pot ammonolysis+aminodefluorination occur in the range from −33 to 5°C.•Temperature of introducing the second amino group is higher by 60–100°C.•Efficient method to prepare high-purity mono- and diaminobenzonitriles was developed.
Polyhalogenated benzotrichlorides (pentafluoro-, chlorotetrafluoro-, chlorotrifluoro-, and tetrafluorobenzotrichlorides) undergo one-pot ammonolysis+aminodefluorination by the action of anhydrous ammonia to form mono- and diamino derivatives of polyhalobenzonitriles. For the substrates comprising halogen at the para-position, the ammonolysis of the CCl3 group and the first aminodefluorination occur simultaneously in the temperature range from −33 to 5°C. The temperature of introducing the second NH2 group is higher by 60–100°C, whereby conditions were found for the selective synthesis of mono- and diaminopolyhalobenzonitriles. The use of anhydrous ammonia as a reagent and a solvent minimizes side reactions and simplifies an isolation of the high purity products.</description><identifier>ISSN: 0022-1139</identifier><identifier>EISSN: 1873-3328</identifier><identifier>DOI: 10.1016/j.jfluchem.2017.06.005</identifier><language>eng</language><publisher>Lausanne: Elsevier B.V</publisher><subject>Aminodefluorination ; Aminopolyhalobenzonitriles ; Ammonia ; Ammonolysis ; Anhydrous ammonia ; CCL3 protein ; Derivatives ; Polyhalobenzotrichlorides ; Side reactions ; Substrates ; Synthesis ; Temperature</subject><ispartof>Journal of fluorine chemistry, 2017-08, Vol.200, p.84-90</ispartof><rights>2017 Elsevier B.V.</rights><rights>Copyright Elsevier BV Aug 2017</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c340t-6b7a1e5f8b9ea288323ff3751c196ea4e2593c892ea82f51bb20cfacdae9fe2f3</citedby><cites>FETCH-LOGICAL-c340t-6b7a1e5f8b9ea288323ff3751c196ea4e2593c892ea82f51bb20cfacdae9fe2f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0022113917302026$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids></links><search><creatorcontrib>Vaganova, Tamara A.</creatorcontrib><creatorcontrib>Rodionov, Vladimir I.</creatorcontrib><creatorcontrib>Chuikov, Igor P.</creatorcontrib><creatorcontrib>Chochrina, Ekaterina A.</creatorcontrib><creatorcontrib>Malykhin, Evgenij V.</creatorcontrib><title>Selective one-pot synthesis of aminopolyhalobenzonitriles from polyhalobenzotrichlorides in anhydrous ammonia</title><title>Journal of fluorine chemistry</title><description>[Display omitted]
•Polyhalogenbenzotrichlorides react with NH3 to form aminopolyhalogenbenzonitriles.•One-pot ammonolysis+aminodefluorination occur in the range from −33 to 5°C.•Temperature of introducing the second amino group is higher by 60–100°C.•Efficient method to prepare high-purity mono- and diaminobenzonitriles was developed.
Polyhalogenated benzotrichlorides (pentafluoro-, chlorotetrafluoro-, chlorotrifluoro-, and tetrafluorobenzotrichlorides) undergo one-pot ammonolysis+aminodefluorination by the action of anhydrous ammonia to form mono- and diamino derivatives of polyhalobenzonitriles. For the substrates comprising halogen at the para-position, the ammonolysis of the CCl3 group and the first aminodefluorination occur simultaneously in the temperature range from −33 to 5°C. The temperature of introducing the second NH2 group is higher by 60–100°C, whereby conditions were found for the selective synthesis of mono- and diaminopolyhalobenzonitriles. The use of anhydrous ammonia as a reagent and a solvent minimizes side reactions and simplifies an isolation of the high purity products.</description><subject>Aminodefluorination</subject><subject>Aminopolyhalobenzonitriles</subject><subject>Ammonia</subject><subject>Ammonolysis</subject><subject>Anhydrous ammonia</subject><subject>CCL3 protein</subject><subject>Derivatives</subject><subject>Polyhalobenzotrichlorides</subject><subject>Side reactions</subject><subject>Substrates</subject><subject>Synthesis</subject><subject>Temperature</subject><issn>0022-1139</issn><issn>1873-3328</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqFkMtKxDAUhoMoOI6-ghRct54k09tOGbyB4EJdhzQ9oSltUpN2oD69HUcXrlydxX_jfIRcUkgo0Oy6TVrdTarBPmFA8wSyBCA9Iita5DzmnBXHZAXAWEwpL0_JWQgtAOSQFyvSv2KHajQ7jJzFeHBjFGY7NhhMiJyOZG-sG1w3N7JzFdpPZ83oTYch0t710R9pEVTTOW_qRTY2kraZa--msNT0S1CekxMtu4AXP3dN3u_v3raP8fPLw9P29jlWfANjnFW5pJjqoipRsqLgjGvN85QqWmYoN8jSkquiZCgLplNaVQyUlqqWWGpkmq_J1aF38O5jwjCK1k3eLpOClilAluWQLq7s4FLeheBRi8GbXvpZUBB7tKIVv2jFHq2ATMB38OYQxOWHnUEvgjJoFdbGLzBF7cx_FV_9gYpO</recordid><startdate>201708</startdate><enddate>201708</enddate><creator>Vaganova, Tamara A.</creator><creator>Rodionov, Vladimir I.</creator><creator>Chuikov, Igor P.</creator><creator>Chochrina, Ekaterina A.</creator><creator>Malykhin, Evgenij V.</creator><general>Elsevier B.V</general><general>Elsevier BV</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7QF</scope><scope>7QO</scope><scope>7QP</scope><scope>7QQ</scope><scope>7SC</scope><scope>7SE</scope><scope>7SP</scope><scope>7SR</scope><scope>7TA</scope><scope>7TB</scope><scope>7U5</scope><scope>7U7</scope><scope>8BQ</scope><scope>8FD</scope><scope>C1K</scope><scope>F28</scope><scope>FR3</scope><scope>H8D</scope><scope>H8G</scope><scope>JG9</scope><scope>JQ2</scope><scope>KR7</scope><scope>L7M</scope><scope>L~C</scope><scope>L~D</scope><scope>P64</scope></search><sort><creationdate>201708</creationdate><title>Selective one-pot synthesis of aminopolyhalobenzonitriles from polyhalobenzotrichlorides in anhydrous ammonia</title><author>Vaganova, Tamara A. ; Rodionov, Vladimir I. ; Chuikov, Igor P. ; Chochrina, Ekaterina A. ; Malykhin, Evgenij V.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c340t-6b7a1e5f8b9ea288323ff3751c196ea4e2593c892ea82f51bb20cfacdae9fe2f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Aminodefluorination</topic><topic>Aminopolyhalobenzonitriles</topic><topic>Ammonia</topic><topic>Ammonolysis</topic><topic>Anhydrous ammonia</topic><topic>CCL3 protein</topic><topic>Derivatives</topic><topic>Polyhalobenzotrichlorides</topic><topic>Side reactions</topic><topic>Substrates</topic><topic>Synthesis</topic><topic>Temperature</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Vaganova, Tamara A.</creatorcontrib><creatorcontrib>Rodionov, Vladimir I.</creatorcontrib><creatorcontrib>Chuikov, Igor P.</creatorcontrib><creatorcontrib>Chochrina, Ekaterina A.</creatorcontrib><creatorcontrib>Malykhin, Evgenij V.</creatorcontrib><collection>CrossRef</collection><collection>Aluminium Industry Abstracts</collection><collection>Biotechnology Research Abstracts</collection><collection>Calcium & Calcified Tissue Abstracts</collection><collection>Ceramic Abstracts</collection><collection>Computer and Information Systems Abstracts</collection><collection>Corrosion Abstracts</collection><collection>Electronics & Communications Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>Materials Business File</collection><collection>Mechanical & Transportation Engineering Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Toxicology Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ANTE: Abstracts in New Technology & Engineering</collection><collection>Engineering Research Database</collection><collection>Aerospace Database</collection><collection>Copper Technical Reference Library</collection><collection>Materials Research Database</collection><collection>ProQuest Computer Science Collection</collection><collection>Civil Engineering Abstracts</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>Computer and Information Systems Abstracts Academic</collection><collection>Computer and Information Systems Abstracts Professional</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Journal of fluorine chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Vaganova, Tamara A.</au><au>Rodionov, Vladimir I.</au><au>Chuikov, Igor P.</au><au>Chochrina, Ekaterina A.</au><au>Malykhin, Evgenij V.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Selective one-pot synthesis of aminopolyhalobenzonitriles from polyhalobenzotrichlorides in anhydrous ammonia</atitle><jtitle>Journal of fluorine chemistry</jtitle><date>2017-08</date><risdate>2017</risdate><volume>200</volume><spage>84</spage><epage>90</epage><pages>84-90</pages><issn>0022-1139</issn><eissn>1873-3328</eissn><abstract>[Display omitted]
•Polyhalogenbenzotrichlorides react with NH3 to form aminopolyhalogenbenzonitriles.•One-pot ammonolysis+aminodefluorination occur in the range from −33 to 5°C.•Temperature of introducing the second amino group is higher by 60–100°C.•Efficient method to prepare high-purity mono- and diaminobenzonitriles was developed.
Polyhalogenated benzotrichlorides (pentafluoro-, chlorotetrafluoro-, chlorotrifluoro-, and tetrafluorobenzotrichlorides) undergo one-pot ammonolysis+aminodefluorination by the action of anhydrous ammonia to form mono- and diamino derivatives of polyhalobenzonitriles. For the substrates comprising halogen at the para-position, the ammonolysis of the CCl3 group and the first aminodefluorination occur simultaneously in the temperature range from −33 to 5°C. The temperature of introducing the second NH2 group is higher by 60–100°C, whereby conditions were found for the selective synthesis of mono- and diaminopolyhalobenzonitriles. The use of anhydrous ammonia as a reagent and a solvent minimizes side reactions and simplifies an isolation of the high purity products.</abstract><cop>Lausanne</cop><pub>Elsevier B.V</pub><doi>10.1016/j.jfluchem.2017.06.005</doi><tpages>7</tpages></addata></record> |
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| subjects | Aminodefluorination Aminopolyhalobenzonitriles Ammonia Ammonolysis Anhydrous ammonia CCL3 protein Derivatives Polyhalobenzotrichlorides Side reactions Substrates Synthesis Temperature |
| title | Selective one-pot synthesis of aminopolyhalobenzonitriles from polyhalobenzotrichlorides in anhydrous ammonia |
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