KR970015581A - 치환된 티아졸 제조 방법 - Google Patents
치환된 티아졸 제조 방법 Download PDFInfo
- Publication number
- KR970015581A KR970015581A KR1019960039421A KR19960039421A KR970015581A KR 970015581 A KR970015581 A KR 970015581A KR 1019960039421 A KR1019960039421 A KR 1019960039421A KR 19960039421 A KR19960039421 A KR 19960039421A KR 970015581 A KR970015581 A KR 970015581A
- Authority
- KR
- South Korea
- Prior art keywords
- process according
- hal
- solvent
- chlorine
- substituted thiazole
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract 5
- 150000003557 thiazoles Chemical class 0.000 title claims 4
- 238000000034 method Methods 0.000 claims abstract 16
- -1 carbonate compound Chemical class 0.000 claims abstract 5
- 229910052801 chlorine Inorganic materials 0.000 claims abstract 4
- 239000003795 chemical substances by application Substances 0.000 claims abstract 3
- 239000000460 chlorine Substances 0.000 claims abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract 2
- 150000002540 isothiocyanates Chemical class 0.000 claims abstract 2
- 239000002904 solvent Substances 0.000 claims 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- 239000012320 chlorinating reagent Substances 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 claims 2
- CFXQEHVMCRXUSD-UHFFFAOYSA-N 1,2,3-Trichloropropane Chemical compound ClCC(Cl)CCl CFXQEHVMCRXUSD-UHFFFAOYSA-N 0.000 claims 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 2
- 238000002425 crystallisation Methods 0.000 claims 2
- 230000008025 crystallization Effects 0.000 claims 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical class C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 claims 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims 1
- 238000004821 distillation Methods 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- VRMUIVKEHJSADG-UHFFFAOYSA-N 2-chloro-5-(chloromethyl)-1,3-thiazole Chemical compound ClCC1=CN=C(Cl)S1 VRMUIVKEHJSADG-UHFFFAOYSA-N 0.000 abstract 1
- 230000031709 bromination Effects 0.000 abstract 1
- 238000005893 bromination reaction Methods 0.000 abstract 1
- 238000005660 chlorination reaction Methods 0.000 abstract 1
- 239000000575 pesticide Substances 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 229940127557 pharmaceutical product Drugs 0.000 abstract 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
치환된 티아졸 제조 방법은 일반식 Hal·CH(R1).CH=C(R2).NCS의 이소티오시아네이트 화합물을 염소화 또는 브롬화제로 용액에서 반응시키는 것으로 이루어진다. 여기서, Hal은 염소 또는 브롬원자이고, R1과 R2는 수소 원자 또는 1 내지 3개의 탄소원자를 포함한 알킬기이다. 농약 및 제약 제품 제조에서 중요한 중간 물질인 화합물 2-클로로-5-(클로로메틸)티아졸은 본 밤법으로 이득이 되게 제조될 수 있다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (15)
- 일반식 Hal·CH(R1).CH=C(R2).NCS의 이소티오시아네이트 화합물을 용액에서 염소화제 또는 브롬화제와 반응시키는 것으로 이루어진 치환된 티아졸 제조 방법. 여기서, Hal은 염소 또는 브롬원자이고 R1과 R2는 수소원자이거나 1 내지 3개의 탄소원자를 포함한 알킬기이다.
- 제1항에 있어서, R1과 R2모두 수소원자임을 특징으로 하는 제조 방법.
- 앞선 청구항 중 어느 항에 있어서, Hal이 염소 원자임을 특징으로 하는 제조 방법.
- 앞선 청구항 중 어느 항에 있어서, 이소티오시아네이트 화합물이 일반식 Hal· CH(R1).CH=C(R2).Hal의 화합물을 알카리금속 티오시아네이트 또는 암모늄티오시아네이트와 반응시킴으로써 제조됨을 특징으로 하는 제조 방법. 여기서 Hal, R1및 R2는 상기 의미와 같다.
- 제4항에 있어서, 이소티오시아네이트 화합물의 제조가 이소티오시아네이트 화합물을 염소화제 또는 브롬화제와 반응시키는데 사용된 것과 같은 용매에서 수행됨을 특징으로 하는 제조 방법.
- 앞선 청구항 중 어느 항에 있어서, 염소화제가 염소 또는 염화설퓨릴임을 특징으로 하는 제조 방법.
- 앞선 청구항 중 어느 항에 있어서, 용매가 지방족 또는 고리지방족 탄화수소이거나 염소화된 탄화수소임을 특징으로 하는 제조 방법.
- 제7항에 있어서, 용매가 헥산 또는 시클로헥산임을 특징으로 하는 제조 방법.
- 제7항에 있어서, 용매가 디클로로메탄, 클로로포름, 1,2-디클로로에탄, 1,1,2-트리클로로에탄, 1,2,3-트리클로로프로판, 1,1,2,2-테트라클로로에탄 또는 클로로벤젠임을 특징으로 하는 제조 방법.
- 제1항 내지 5항 중 어느 항에 있어서, 용매가 1,2-디클로로에탄이고 염소화제가 염화설퓨릴임을 특징으로 하는 제조 방법.
- 앞선 청구항 중 어느 항에 있어서, 반응이 -40 내지 50℃의 온도에서 수행됨을 특징으로 하는 제조 방법.
- 제11항에 있어서, 온도가 -25 내지 0℃임을 특징으로 하는 제조 방법,
- 앞선 청구항 중 어느 항에 있어서, 제조된 치환된 티아졸이 증류 또는 결정화에 의해 반응혼합물로부터 분리됨을 특징으로 하는 제조 방법.
- 제1항 내지 12항 중 어느 항에 있어서, 생성된 치환된 티아졸이 염으로 전환되어서 이 형태로 결정화에 의해 분리됨을 특징으로 하는 제조 방법.
- 실시예들중의 어느 하나에 따르는 치환된 티아졸 제조 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9518824.9 | 1995-09-14 | ||
| GBGB9518824.9A GB9518824D0 (en) | 1995-09-14 | 1995-09-14 | Preparation of substituted thiazoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR970015581A true KR970015581A (ko) | 1997-04-28 |
Family
ID=10780723
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019960039421A KR970015581A (ko) | 1995-09-14 | 1996-09-12 | 치환된 티아졸 제조 방법 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US5705652A (ko) |
| EP (1) | EP0763531B1 (ko) |
| JP (1) | JP3168319B2 (ko) |
| KR (1) | KR970015581A (ko) |
| CN (1) | CN1064961C (ko) |
| AT (1) | ATE190975T1 (ko) |
| CA (1) | CA2186167C (ko) |
| DE (1) | DE69607272T2 (ko) |
| DK (1) | DK0763531T3 (ko) |
| ES (1) | ES2144700T3 (ko) |
| FI (1) | FI119244B (ko) |
| GB (1) | GB9518824D0 (ko) |
| GR (1) | GR3033620T3 (ko) |
| HU (1) | HU224038B1 (ko) |
| IN (1) | IN183678B (ko) |
| NO (1) | NO306298B1 (ko) |
| PT (1) | PT763531E (ko) |
| TW (1) | TW355708B (ko) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IN182219B (ko) * | 1996-02-21 | 1999-02-06 | Kuraray Co | |
| WO1998045279A1 (en) * | 1997-04-07 | 1998-10-15 | Reilly Industries, Inc. | Preparation of thiazoles using 1,3-dihalopropenes |
| US5932736A (en) * | 1997-04-07 | 1999-08-03 | Reilly Industries, Inc. | Preparation of heterocycles using 1,3-dihalopropenes |
| US5959118A (en) * | 1997-08-29 | 1999-09-28 | Abbott Laboratories | Process for the preparation of 5-hydroxymethylthiazoles |
| DE19908447A1 (de) | 1999-02-26 | 2000-08-31 | Bayer Ag | Verfahren zur Herstellung von 2-Chlor-5-chlormethylthiazol |
| WO2001036400A1 (de) * | 1999-11-15 | 2001-05-25 | Dsm Fine Chemicals Austria Nfg Gmbh & Cokg | Verfahren zur herstellung von 2-chlor-5-chlormethyl-1,3-thiazol |
| AT409760B (de) * | 1999-11-15 | 2002-11-25 | Dsm Fine Chem Austria Gmbh | Verfahren zur herstellung von 2-chlor-5-chlormethyl-1,3-thiazol |
| AT408756B (de) * | 2000-05-23 | 2002-03-25 | Dsm Fine Chem Austria Gmbh | Verfahren zur herstellung von 2-chlor-5-chlormethyl-1,3-thiazol |
| MXPA03001179A (es) * | 2000-08-10 | 2003-06-30 | Bayer Cropscience Ag | Modelo industrial de cinturon tequilero. |
| DE10061083A1 (de) | 2000-12-08 | 2002-06-13 | Bayer Ag | Bis-(2-chlor-thiazolyl-5-methyl)-amin und seine Salze sowie Verfahren zur Aufarbeitung von 5-Aminomethyl-2-chlor-thiazol und Bis-(2-chlor-thiazol-5-methyl)-amin enthaltenden Reaktionsgemischen |
| EP1728787B1 (en) | 2004-03-22 | 2011-01-26 | Toyo Boseki Kabushiki Kaisha | Process for purification of 2-chloro-5-chloromethyl -1,3-thiazole |
| CN102503872A (zh) * | 2011-12-15 | 2012-06-20 | 常州大学 | 一种制备异硫氰酸酯的方法 |
| CN103772315B (zh) * | 2014-01-07 | 2015-10-21 | 山东汇海医药化工有限公司 | 一种一步合成4-甲基噻唑-5-甲酸乙酯的方法 |
| CN103755661B (zh) * | 2014-02-08 | 2016-09-21 | 山东省农药科学研究院 | 一种2-氯-5-氯甲基噻唑的分离精制方法 |
| TWI620558B (zh) | 2016-12-20 | 2018-04-11 | 富伯生醫科技股份有限公司 | 穿戴式手部復健輔具系統 |
| CN109293596A (zh) * | 2018-09-30 | 2019-02-01 | 江苏润泽鑫生物科技有限公司 | 2-氯-5-氯甲基噻唑的制备方法 |
| CN113121465A (zh) * | 2021-05-28 | 2021-07-16 | 安徽海顺化工有限公司 | 一种2-氯-5-氯甲基噻唑的合成工艺 |
| KR102610076B1 (ko) * | 2022-04-29 | 2023-12-04 | 윤필영 | 쿨링 기능성 퀼팅 덮는 이불 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3631538A1 (de) * | 1986-09-17 | 1988-03-24 | Bayer Ag | Verfahren zur herstellung von 2-chlor-5-chlormethylthiazol |
| US5180833A (en) * | 1990-03-16 | 1993-01-19 | Takeda Chemical Industries, Ltd. | Process for the preparation of chlorothiazole derivatives |
-
1995
- 1995-09-14 GB GBGB9518824.9A patent/GB9518824D0/en active Pending
-
1996
- 1996-08-26 IN IN1508CA1996 patent/IN183678B/en unknown
- 1996-08-27 FI FI963344A patent/FI119244B/fi active IP Right Grant
- 1996-08-28 EP EP96306214A patent/EP0763531B1/en not_active Expired - Lifetime
- 1996-08-28 ES ES96306214T patent/ES2144700T3/es not_active Expired - Lifetime
- 1996-08-28 DE DE69607272T patent/DE69607272T2/de not_active Expired - Lifetime
- 1996-08-28 PT PT96306214T patent/PT763531E/pt unknown
- 1996-08-28 AT AT96306214T patent/ATE190975T1/de not_active IP Right Cessation
- 1996-08-28 DK DK96306214T patent/DK0763531T3/da active
- 1996-09-09 US US08/711,228 patent/US5705652A/en not_active Expired - Lifetime
- 1996-09-12 KR KR1019960039421A patent/KR970015581A/ko active IP Right Grant
- 1996-09-13 HU HU9602510A patent/HU224038B1/hu not_active IP Right Cessation
- 1996-09-13 CA CA002186167A patent/CA2186167C/en not_active Expired - Fee Related
- 1996-09-13 NO NO963829A patent/NO306298B1/no not_active IP Right Cessation
- 1996-09-13 JP JP24285196A patent/JP3168319B2/ja not_active Expired - Fee Related
- 1996-09-14 TW TW085111252A patent/TW355708B/zh not_active IP Right Cessation
- 1996-09-16 CN CN961134194A patent/CN1064961C/zh not_active Expired - Fee Related
-
2000
- 2000-06-07 GR GR20000401306T patent/GR3033620T3/el not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FI119244B (fi) | 2008-09-15 |
| DE69607272D1 (de) | 2000-04-27 |
| HUP9602510A3 (en) | 1999-03-29 |
| HU9602510D0 (en) | 1996-11-28 |
| FI963344A (fi) | 1997-03-15 |
| DE69607272T2 (de) | 2000-07-13 |
| ES2144700T3 (es) | 2000-06-16 |
| IN183678B (ko) | 2000-03-18 |
| TW355708B (en) | 1999-04-11 |
| NO963829L (no) | 1997-03-17 |
| ATE190975T1 (de) | 2000-04-15 |
| JPH09110844A (ja) | 1997-04-28 |
| EP0763531A1 (en) | 1997-03-19 |
| FI963344A0 (fi) | 1996-08-27 |
| PT763531E (pt) | 2000-08-31 |
| DK0763531T3 (da) | 2000-07-10 |
| CA2186167A1 (en) | 1997-03-15 |
| JP3168319B2 (ja) | 2001-05-21 |
| CN1064961C (zh) | 2001-04-25 |
| NO963829D0 (no) | 1996-09-13 |
| GB9518824D0 (en) | 1995-11-15 |
| HU224038B1 (hu) | 2005-05-30 |
| CA2186167C (en) | 2007-07-24 |
| US5705652A (en) | 1998-01-06 |
| CN1152571A (zh) | 1997-06-25 |
| EP0763531B1 (en) | 2000-03-22 |
| NO306298B1 (no) | 1999-10-18 |
| HUP9602510A1 (en) | 1997-05-28 |
| GR3033620T3 (en) | 2000-10-31 |
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| A201 | Request for examination | ||
| E902 | Notification of reason for refusal | ||
| E701 | Decision to grant or registration of patent right | ||
| NORF | Unpaid initial registration fee |