CA2155715A1 - Preparation of thioamides - Google Patents
Preparation of thioamidesInfo
- Publication number
- CA2155715A1 CA2155715A1 CA002155715A CA2155715A CA2155715A1 CA 2155715 A1 CA2155715 A1 CA 2155715A1 CA 002155715 A CA002155715 A CA 002155715A CA 2155715 A CA2155715 A CA 2155715A CA 2155715 A1 CA2155715 A1 CA 2155715A1
- Authority
- CA
- Canada
- Prior art keywords
- denotes
- carbon atoms
- alkyl radical
- radical containing
- isopropylamine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 238000002360 preparation method Methods 0.000 title claims description 10
- 150000003556 thioamides Chemical class 0.000 title description 8
- -1 nitrile compound Chemical class 0.000 claims abstract description 21
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 239000002798 polar solvent Substances 0.000 claims abstract description 7
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims abstract description 6
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000005840 aryl radicals Chemical class 0.000 claims abstract description 3
- 125000001931 aliphatic group Chemical group 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 150000002825 nitriles Chemical class 0.000 claims description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 8
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 6
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 6
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 claims description 6
- NPCLRBQYESMUPD-UHFFFAOYSA-N 2-methylpropanethioamide Chemical compound CC(C)C(N)=S NPCLRBQYESMUPD-UHFFFAOYSA-N 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229960001760 dimethyl sulfoxide Drugs 0.000 claims description 4
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 claims description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000003518 caustics Substances 0.000 description 3
- 239000013557 residual solvent Substances 0.000 description 3
- 150000001408 amides Chemical group 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- WPZSAUFQHYFIPG-UHFFFAOYSA-N propanethioamide Chemical compound CCC(N)=S WPZSAUFQHYFIPG-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/38—Amides of thiocarboxylic acids
- C07C327/40—Amides of thiocarboxylic acids having carbon atoms of thiocarboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C327/42—Amides of thiocarboxylic acids having carbon atoms of thiocarboxamide groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of a saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/38—Amides of thiocarboxylic acids
- C07C327/40—Amides of thiocarboxylic acids having carbon atoms of thiocarboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9416364A GB9416364D0 (en) | 1994-08-12 | 1994-08-12 | Preparation of thioamides |
| GB9416364.9 | 1994-08-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2155715A1 true CA2155715A1 (en) | 1996-02-13 |
Family
ID=10759812
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002155715A Abandoned CA2155715A1 (en) | 1994-08-12 | 1995-08-09 | Preparation of thioamides |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US5723663A (enEXAMPLES) |
| EP (1) | EP0696581B1 (enEXAMPLES) |
| JP (1) | JPH0892202A (enEXAMPLES) |
| AT (1) | ATE162517T1 (enEXAMPLES) |
| CA (1) | CA2155715A1 (enEXAMPLES) |
| DE (1) | DE69501487T2 (enEXAMPLES) |
| DK (1) | DK0696581T3 (enEXAMPLES) |
| ES (1) | ES2113713T3 (enEXAMPLES) |
| FI (1) | FI120767B (enEXAMPLES) |
| GB (2) | GB9416364D0 (enEXAMPLES) |
| GR (1) | GR3026439T3 (enEXAMPLES) |
| HU (1) | HU214221B (enEXAMPLES) |
| IN (1) | IN179110B (enEXAMPLES) |
| NO (1) | NO305118B1 (enEXAMPLES) |
| TW (1) | TW328077B (enEXAMPLES) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6380393B1 (en) | 1999-03-19 | 2002-04-30 | San Diego State University Foundation | Ligands, transition metal complexes and methods of using same |
| US6627758B2 (en) | 1999-03-19 | 2003-09-30 | San Diego State University Foundation | Compositions and methods for hydration of terminal alkynes |
| US6541667B1 (en) | 2001-12-17 | 2003-04-01 | Bayer Corporation | Methods for preparation of thioamides |
| WO2008013622A2 (en) | 2006-07-27 | 2008-01-31 | E. I. Du Pont De Nemours And Company | Fungicidal azocyclic amides |
| AU2009206468B2 (en) | 2008-01-25 | 2014-01-09 | E. I. Du Pont De Nemours And Company | Fungicidal heterocyclic compounds |
| TW201036966A (en) | 2008-12-02 | 2010-10-16 | Du Pont | Fungicidal heterocyclic compounds |
| US20130045948A1 (en) | 2009-12-11 | 2013-02-21 | E I Du Pont De Nemours And Company | Azocyclic inhibitors of fatty acid amide hydrolase |
| US8835427B2 (en) | 2010-01-07 | 2014-09-16 | E I Du Pont De Nemours And Company | Fungicidal heterocyclic compounds |
| CN102933577B (zh) | 2010-05-20 | 2014-08-06 | 纳幕尔杜邦公司 | 杀真菌的肟和腙 |
| KR20140017520A (ko) | 2010-12-17 | 2014-02-11 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 살진균제 아조사이클릭 아미드 |
| JP5896521B2 (ja) * | 2012-01-31 | 2016-03-30 | 住友精化株式会社 | ２，２−ジメチルプロパンチオアミドの製造方法 |
| JP6700292B2 (ja) * | 2015-03-05 | 2020-05-27 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | ピペリジン−４−カルボチオアミド塩酸塩を調製する方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2201170A (en) * | 1938-09-15 | 1940-05-21 | Du Pont | Secondary thioamides and process of preparing them |
| US3274243A (en) * | 1963-02-07 | 1966-09-20 | Allied Chem | Preparation of alkanoic thioamides |
| US3700664A (en) * | 1970-03-26 | 1972-10-24 | Uniroyal Ltd | Preparation of thionamides |
-
1994
- 1994-08-12 GB GB9416364A patent/GB9416364D0/en active Pending
-
1995
- 1995-07-31 IN IN882CA1995 patent/IN179110B/en unknown
- 1995-08-01 FI FI953673A patent/FI120767B/fi active IP Right Grant
- 1995-08-04 EP EP95305466A patent/EP0696581B1/en not_active Expired - Lifetime
- 1995-08-04 DK DK95305466.5T patent/DK0696581T3/da active
- 1995-08-04 GB GB9516037A patent/GB2292379B/en not_active Expired - Fee Related
- 1995-08-04 ES ES95305466T patent/ES2113713T3/es not_active Expired - Lifetime
- 1995-08-04 AT AT95305466T patent/ATE162517T1/de not_active IP Right Cessation
- 1995-08-04 DE DE69501487T patent/DE69501487T2/de not_active Expired - Lifetime
- 1995-08-08 TW TW084108243A patent/TW328077B/zh not_active IP Right Cessation
- 1995-08-08 US US08/512,662 patent/US5723663A/en not_active Expired - Lifetime
- 1995-08-09 CA CA002155715A patent/CA2155715A1/en not_active Abandoned
- 1995-08-10 JP JP7204154A patent/JPH0892202A/ja active Pending
- 1995-08-10 NO NO953139A patent/NO305118B1/no not_active IP Right Cessation
- 1995-08-11 HU HU9502373A patent/HU214221B/hu not_active IP Right Cessation
-
1998
- 1998-03-24 GR GR980400627T patent/GR3026439T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0696581B1 (en) | 1998-01-21 |
| DK0696581T3 (da) | 1998-04-14 |
| US5723663A (en) | 1998-03-03 |
| TW328077B (en) | 1998-03-11 |
| HU214221B (hu) | 1998-01-28 |
| NO953139L (no) | 1996-02-13 |
| IN179110B (enEXAMPLES) | 1997-08-23 |
| GB9516037D0 (en) | 1995-10-04 |
| NO305118B1 (no) | 1999-04-06 |
| DE69501487D1 (de) | 1998-02-26 |
| FI953673L (fi) | 1996-02-13 |
| ATE162517T1 (de) | 1998-02-15 |
| GB2292379A (en) | 1996-02-21 |
| ES2113713T3 (es) | 1998-05-01 |
| EP0696581A3 (enEXAMPLES) | 1996-03-20 |
| GB2292379B (en) | 1998-02-18 |
| NO953139D0 (no) | 1995-08-10 |
| HU9502373D0 (en) | 1995-10-30 |
| FI953673A0 (fi) | 1995-08-01 |
| DE69501487T2 (de) | 1998-07-16 |
| FI120767B (fi) | 2010-02-26 |
| JPH0892202A (ja) | 1996-04-09 |
| EP0696581A2 (en) | 1996-02-14 |
| HUT71988A (en) | 1996-03-28 |
| GB9416364D0 (en) | 1994-10-05 |
| GR3026439T3 (en) | 1998-06-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |