JP5235366B2 - 芳香族またはヘテロ芳香族ニトリルを触媒的に調製するための方法 - Google Patents
芳香族またはヘテロ芳香族ニトリルを触媒的に調製するための方法 Download PDFInfo
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- JP5235366B2 JP5235366B2 JP2007234347A JP2007234347A JP5235366B2 JP 5235366 B2 JP5235366 B2 JP 5235366B2 JP 2007234347 A JP2007234347 A JP 2007234347A JP 2007234347 A JP2007234347 A JP 2007234347A JP 5235366 B2 JP5235366 B2 JP 5235366B2
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- alkyl
- copper
- cyanide
- aromatic
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/14—Preparation of carboxylic acid nitriles by reaction of cyanides with halogen-containing compounds with replacement of halogen atoms by cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Toxicology (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Indole Compounds (AREA)
Description
Ar−CN (I)
の、場合によっては置換された芳香族またはヘテロ芳香族ニトリルを触媒的に調製するための方法において、
一般式(II)
Ar−X (II)
[式中、Xは、塩素、臭素、ヨウ素もしくはスルホネート、好ましくは塩素および臭素、より好ましくは臭素であり、Arは、場合によっては置換された芳香族またはヘテロ芳香族基である]の対応するハロゲン化アリールを、銅化合物と1〜3個の窒素原子を有する単座の5員〜6員環ヘテロ芳香族アミンとの存在下に、シアニド供与体としてのヘキサシアノ鉄(II)酸カリウムまたはヘキサシアノ鉄(III)酸カリウムと反応させることにより実施する。
一般的手順:
オートクレーブ中で、1当量のハロゲン化アリールもしくはヘテロハロゲン化アリール(heteroaryl halide)、2当量の1−アルキルイミダゾール、0.1当量のCuI、0.2当量の乾燥K4[Fe(CN)6](ヘキサシアノ鉄(II)酸カリウム)、GC分析のための内部標準としてのテトラデカン、および適切な量のトルエンをアルゴン雰囲気下で組合せ、160℃に加熱した。(そのK4[Fe(CN)6]は、粉体状のK4[Fe(CN)6]・3H2Oを、1mbar以下の真空中80℃で少なくとも24時間加熱することにより乾燥させた)。16時間後に、その反応混合物を冷却して、室温とした。転化率と収率はガスクロマトグラフィーによって測定した。慣用される作業(蒸留、結晶化またはクロマトグラフィー)に従って、生成物の単離を行った。
Claims (1)
- 一般式(I)
Ar−CN (I)
の、場合によっては置換された芳香族またはヘテロ芳香族ニトリルを、
一般式(II)
Ar−X (II)
[式中、Xは塩素、臭素、ヨウ素またはスルホネートであり、Arは、場合によっては置換された芳香族またはヘテロ芳香族基である]の対応するハロゲン化アリールをシアニド供与体と反応させることによって、触媒的に調製するための方法であって、
銅化合物の存在下、ならびに1−メチルイミダゾール、1−エチルイミダゾール、1−プロピルイミダゾール、1−イソプロピルイミダゾール、1−ブチルイミダゾール、1−sec−ブチルイミダゾール及び1−tert−ブチルイミダゾールからなる群より選択されるアルキル置換イミダゾールの存在下に前記反応を実施し、使用されるシアニド供与体がヘキサシアノ鉄(II)酸カリウムまたはヘキサシアノ鉄(III)酸カリウムであることを特徴とする、方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102006042439A DE102006042439A1 (de) | 2006-09-09 | 2006-09-09 | Verfahren zur katalytischen Herstellung von aromatischen oder heteroaromatischen Nitrilen |
DE102006042439.5 | 2006-09-09 |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2008063336A JP2008063336A (ja) | 2008-03-21 |
JP2008063336A5 JP2008063336A5 (ja) | 2010-09-30 |
JP5235366B2 true JP5235366B2 (ja) | 2013-07-10 |
Family
ID=38924443
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2007234347A Expired - Fee Related JP5235366B2 (ja) | 2006-09-09 | 2007-09-10 | 芳香族またはヘテロ芳香族ニトリルを触媒的に調製するための方法 |
Country Status (6)
Country | Link |
---|---|
US (1) | US7592452B2 (ja) |
EP (1) | EP1903030B1 (ja) |
JP (1) | JP5235366B2 (ja) |
DE (1) | DE102006042439A1 (ja) |
ES (1) | ES2492918T3 (ja) |
PL (1) | PL1903030T3 (ja) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI432421B (zh) | 2007-12-19 | 2014-04-01 | Du Pont | 製備2-胺基-5-氰基苯甲酸衍生物之方法 |
TWI431000B (zh) * | 2008-03-05 | 2014-03-21 | Du Pont | 製備2-胺基-5-氰基苯甲酸衍生物之方法 |
CN101671300B (zh) * | 2009-09-28 | 2011-04-13 | 南京第一农药集团有限公司 | 一种2-氰基-3,6-二氯吡啶的制备方法 |
CN102381918B (zh) * | 2011-08-31 | 2014-03-26 | 河南科技大学 | 一种由苄氯类化合物合成苯乙腈类化合物的方法 |
GB201118876D0 (en) | 2011-11-01 | 2011-12-14 | Astex Therapeutics Ltd | Pharmaceutical compounds |
CN102408378A (zh) * | 2012-01-06 | 2012-04-11 | 盛世泰科生物医药技术(苏州)有限公司 | 一种5-氰基嘧啶的合成方法 |
CN104755473B (zh) | 2012-08-16 | 2017-03-08 | 拜耳医药股份有限公司 | 2,3‑苯并二氮杂* |
CN102898264B (zh) * | 2012-09-12 | 2014-07-02 | 浙江大学 | 一种芳香腈或杂芳腈的催化制备工艺 |
CN107903190A (zh) * | 2017-12-14 | 2018-04-13 | 郑州盖科科技有限公司 | 一种对叔丁基邻苯二甲腈的制备方法 |
CN109369563A (zh) * | 2018-12-10 | 2019-02-22 | 白东跃 | 一种医药中间体2-氰基噻唑的制备方法 |
CN114380713A (zh) * | 2021-09-29 | 2022-04-22 | 辽宁众辉生物科技有限公司 | 邻甲基苯甲酰氰合成方法 |
WO2023217989A1 (en) | 2022-05-12 | 2023-11-16 | Syngenta Crop Protection Ag | Alkoxy heteroaryl- carboxamide or thioamide compounds |
CN115677522A (zh) * | 2022-10-31 | 2023-02-03 | 浙江巍华新材料股份有限公司 | 一种邻三氟甲基苯甲酰胺及其中间体的制备方法 |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
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DE293094C (ja) | ||||
US4211721A (en) | 1978-12-04 | 1980-07-08 | Hooker Chemicals & Plastics Corp. | Process for the preparation of aromatic nitriles |
JPS55120549A (en) * | 1979-03-09 | 1980-09-17 | Nippon Kayaku Co Ltd | Preparation of 2-chloro-6-nitrobenzonitrile |
US4499025A (en) | 1982-04-23 | 1985-02-12 | Occidental Chemical Corporation | Electrochemical maintenance of catalyst activity |
BR9509373A (pt) | 1994-10-17 | 1998-07-07 | Novartis Ag | Processo para a preparação de 3- aminobenzonitrilas substituídas |
DE19706648A1 (de) | 1997-02-20 | 1998-08-27 | Bayer Ag | Verfahren zur Herstellung von aromatischen Nitrilen |
EP0994099B1 (en) | 1998-10-13 | 2005-02-02 | Bayer CropScience S.A. | Process for preparing 4-cyano-3-nitrobenzotrifluoride from 3-bromo-4-cyanobenzotrifluoride in the presence of catalytic cuprous cyanide and a phase transfer catalyst. |
JP2000344732A (ja) * | 1999-03-29 | 2000-12-12 | Nissan Chem Ind Ltd | ベンゾニトリル化合物の製造法 |
DE10113976A1 (de) | 2001-03-22 | 2002-09-26 | Degussa | Verfahren zur katalytischen Herstellung von aromatischen oder heteroaromatischen Nitrilen |
DE10322408A1 (de) | 2003-05-16 | 2004-12-02 | Degussa Ag | Stickstoffhaltige monodentate Phosphine und deren Verwendung in der Katalyse |
DE102005009517A1 (de) | 2005-02-28 | 2006-08-31 | Lanxess Deutschland Gmbh | Verfahren zur katalytischen Herstellung von aromatischen Nitrilen |
-
2006
- 2006-09-09 DE DE102006042439A patent/DE102006042439A1/de not_active Withdrawn
-
2007
- 2007-08-27 US US11/895,728 patent/US7592452B2/en not_active Expired - Fee Related
- 2007-08-31 EP EP07115366.2A patent/EP1903030B1/de not_active Not-in-force
- 2007-08-31 ES ES07115366.2T patent/ES2492918T3/es active Active
- 2007-08-31 PL PL07115366T patent/PL1903030T3/pl unknown
- 2007-09-10 JP JP2007234347A patent/JP5235366B2/ja not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
PL1903030T3 (pl) | 2014-11-28 |
US7592452B2 (en) | 2009-09-22 |
JP2008063336A (ja) | 2008-03-21 |
ES2492918T3 (es) | 2014-09-10 |
US20090062541A1 (en) | 2009-03-05 |
EP1903030B1 (de) | 2014-06-04 |
EP1903030A1 (de) | 2008-03-26 |
DE102006042439A1 (de) | 2008-03-27 |
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