DE3234530A1 - Verfahren zur herstellung von 2-chlorbenzthiazol - Google Patents
Verfahren zur herstellung von 2-chlorbenzthiazolInfo
- Publication number
- DE3234530A1 DE3234530A1 DE19823234530 DE3234530A DE3234530A1 DE 3234530 A1 DE3234530 A1 DE 3234530A1 DE 19823234530 DE19823234530 DE 19823234530 DE 3234530 A DE3234530 A DE 3234530A DE 3234530 A1 DE3234530 A1 DE 3234530A1
- Authority
- DE
- Germany
- Prior art keywords
- chlorobenzothiazole
- chlorine
- benzothiazole
- chlorobenzene
- chloride
- 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.)
- Withdrawn
Links
- BSQLQMLFTHJVKS-UHFFFAOYSA-N 2-chloro-1,3-benzothiazole Chemical compound C1=CC=C2SC(Cl)=NC2=C1 BSQLQMLFTHJVKS-UHFFFAOYSA-N 0.000 title claims description 22
- 238000004519 manufacturing process Methods 0.000 title description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 36
- 239000000460 chlorine Substances 0.000 claims description 21
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 20
- 229910052801 chlorine Inorganic materials 0.000 claims description 20
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 12
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 10
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 10
- 238000005660 chlorination reaction Methods 0.000 claims description 9
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 6
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- CMLFFNZGVZXDDW-UHFFFAOYSA-N pyridine;trichlorophosphane Chemical compound ClP(Cl)Cl.C1=CC=NC=C1 CMLFFNZGVZXDDW-UHFFFAOYSA-N 0.000 claims 1
- 238000004821 distillation Methods 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- DRNNMKBEVALIPU-UHFFFAOYSA-N 1-chloro-2-isocyanobenzene Chemical compound ClC1=CC=CC=C1[N+]#[C-] DRNNMKBEVALIPU-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- IJCVBMSXIPFVLH-UHFFFAOYSA-N [C].S=O Chemical compound [C].S=O IJCVBMSXIPFVLH-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 229960004275 glycolic acid Drugs 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- XIGAUIHYSDTJHW-UHFFFAOYSA-N mefenacet Chemical compound N=1C2=CC=CC=C2SC=1OCC(=O)N(C)C1=CC=CC=C1 XIGAUIHYSDTJHW-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000009183 running Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical class ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 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
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Catalysts (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823234530 DE3234530A1 (de) | 1982-09-17 | 1982-09-17 | Verfahren zur herstellung von 2-chlorbenzthiazol |
| US06/526,932 US4764621A (en) | 1982-09-17 | 1983-08-26 | Preparation of 2-chlorobenzthiazole |
| DE8383108845T DE3378316D1 (en) | 1982-09-17 | 1983-09-08 | Process for the preparation of 2-chloro-benzothiazole |
| EP83108845A EP0103817B1 (de) | 1982-09-17 | 1983-09-08 | Verfahren zur Herstellung von 2-Chlorbenzthiazol |
| JP58167658A JPS5970677A (ja) | 1982-09-17 | 1983-09-13 | ２−クロロベンズチアゾ−ルの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823234530 DE3234530A1 (de) | 1982-09-17 | 1982-09-17 | Verfahren zur herstellung von 2-chlorbenzthiazol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3234530A1 true DE3234530A1 (de) | 1984-03-22 |
Family
ID=6173504
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19823234530 Withdrawn DE3234530A1 (de) | 1982-09-17 | 1982-09-17 | Verfahren zur herstellung von 2-chlorbenzthiazol |
| DE8383108845T Expired DE3378316D1 (en) | 1982-09-17 | 1983-09-08 | Process for the preparation of 2-chloro-benzothiazole |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8383108845T Expired DE3378316D1 (en) | 1982-09-17 | 1983-09-08 | Process for the preparation of 2-chloro-benzothiazole |
Country Status (4)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999031076A1 (de) * | 1997-12-16 | 1999-06-24 | Aventis Cropscience Gmbh | Verfahren zur herstellung von chlorbenzoxazolen |
| CN109456282A (zh) * | 2019-01-11 | 2019-03-12 | 江苏快达农化股份有限公司 | 一种2-氯苯并噻唑的合成方法 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61106563A (ja) * | 1984-10-30 | 1986-05-24 | Oouchi Shinko Kagaku Kogyo Kk | ２−クロルベンゾチアゾ−ル誘導体の製造方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1670453A1 (de) * | 1967-08-02 | 1971-02-11 | Cassella Farbwerke Mainkur Ag | Verfahren zur Herstellung von 2-Chlorbenzthiazolen |
| DE3018088A1 (de) * | 1980-05-12 | 1981-11-19 | Cassella Ag, 6000 Frankfurt | Verfahren zur herstellung von 2-chlorbenzothiazol |
| DE3023227A1 (de) * | 1980-06-21 | 1982-01-07 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von 2-chlor-benzthiazolen |
-
1982
- 1982-09-17 DE DE19823234530 patent/DE3234530A1/de not_active Withdrawn
-
1983
- 1983-08-26 US US06/526,932 patent/US4764621A/en not_active Expired - Lifetime
- 1983-09-08 EP EP83108845A patent/EP0103817B1/de not_active Expired
- 1983-09-08 DE DE8383108845T patent/DE3378316D1/de not_active Expired
- 1983-09-13 JP JP58167658A patent/JPS5970677A/ja active Granted
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999031076A1 (de) * | 1997-12-16 | 1999-06-24 | Aventis Cropscience Gmbh | Verfahren zur herstellung von chlorbenzoxazolen |
| US6274739B1 (en) | 1997-12-16 | 2001-08-14 | Aventis Cropscience Gmbh | Method for producing chlorobenzoxazolene |
| AU761589B2 (en) * | 1997-12-16 | 2003-06-05 | Bayer Intellectual Property Gmbh | Method for producing chlorobenzoxazolene |
| CZ297899B6 (cs) * | 1997-12-16 | 2007-04-25 | Aventis Cropscience Gmbh | Zpusob výroby chlorbenzoxazolu |
| CN109456282A (zh) * | 2019-01-11 | 2019-03-12 | 江苏快达农化股份有限公司 | 一种2-氯苯并噻唑的合成方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0103817B1 (de) | 1988-10-26 |
| JPH0534355B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1993-05-21 |
| EP0103817A2 (de) | 1984-03-28 |
| JPS5970677A (ja) | 1984-04-21 |
| EP0103817A3 (en) | 1985-10-30 |
| US4764621A (en) | 1988-08-16 |
| DE3378316D1 (en) | 1988-12-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |