BE897750A - Procede de preparation de 2-chorobenzthiazole a partir de 2-mercaptobenzthiazole - Google Patents
Procede de preparation de 2-chorobenzthiazole a partir de 2-mercaptobenzthiazole Download PDFInfo
- Publication number
- BE897750A BE897750A BE0/211528A BE211528A BE897750A BE 897750 A BE897750 A BE 897750A BE 0/211528 A BE0/211528 A BE 0/211528A BE 211528 A BE211528 A BE 211528A BE 897750 A BE897750 A BE 897750A
- Authority
- BE
- Belgium
- Prior art keywords
- chlorobenzthiazole
- mercaptobenzthiazole
- preparation
- phosphorus
- reaction
- Prior art date
Links
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 238000000034 method Methods 0.000 title claims description 13
- BSQLQMLFTHJVKS-UHFFFAOYSA-N 2-chloro-1,3-benzothiazole Chemical compound C1=CC=C2SC(Cl)=NC2=C1 BSQLQMLFTHJVKS-UHFFFAOYSA-N 0.000 claims abstract description 19
- WQYSXVGEZYESBR-UHFFFAOYSA-N thiophosphoryl chloride Chemical compound ClP(Cl)(Cl)=S WQYSXVGEZYESBR-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000000460 chlorine Substances 0.000 claims abstract description 11
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 9
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 5
- 239000003054 catalyst Substances 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 239000006227 byproduct Substances 0.000 claims description 4
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 3
- 238000005660 chlorination reaction Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000004009 herbicide Substances 0.000 abstract description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- JJWKPURADFRFRB-UHFFFAOYSA-N carbonyl sulfide Chemical compound O=C=S JJWKPURADFRFRB-UHFFFAOYSA-N 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 239000011814 protection agent Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 101001076732 Homo sapiens RNA-binding protein 27 Proteins 0.000 description 1
- 229910018894 PSCl3 Inorganic materials 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 102100025873 RNA-binding protein 27 Human genes 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- -1 benzthiazol-2-yloxy Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 229960004275 glycolic acid Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- KLBOFRLEHJAXIU-UHFFFAOYSA-N tributylazanium;chloride Chemical compound Cl.CCCCN(CCCC)CCCC KLBOFRLEHJAXIU-UHFFFAOYSA-N 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)
- Thiazole And Isothizaole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823234531 DE3234531A1 (de) | 1982-09-17 | 1982-09-17 | Verfahren zur herstellung von 2-chlorbenzthiazol aus 2-mercaptobenzthiazol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE897750A true BE897750A (fr) | 1984-03-14 |
Family
ID=6173505
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE0/211528A BE897750A (fr) | 1982-09-17 | 1983-09-14 | Procede de preparation de 2-chorobenzthiazole a partir de 2-mercaptobenzthiazole |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS5970678A (enrdf_load_stackoverflow) |
| BE (1) | BE897750A (enrdf_load_stackoverflow) |
| DE (1) | DE3234531A1 (enrdf_load_stackoverflow) |
Families Citing this family (4)
| 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 |
| JPH0711695B2 (ja) | 1985-09-25 | 1995-02-08 | 富士写真フイルム株式会社 | 撮影用ハロゲン化銀カラー感光材料の処理方法 |
| JPH01133904A (ja) * | 1987-07-17 | 1989-05-26 | Nisshin Steel Co Ltd | 各種形状の超電導体の作製法 |
| ES2156131T3 (es) * | 1993-04-27 | 2001-06-16 | Bayer Ag | Procedimiento para la obtencion de 2-cloro-benzotiazoles o de 2-clorobenzoxazoles. |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE516998C (de) * | 1928-05-01 | 1931-02-05 | I G Farbenindustrie Akt Ges | Verfahren zur Darstellung der 2-Chlorbenzothiazole |
-
1982
- 1982-09-17 DE DE19823234531 patent/DE3234531A1/de active Granted
-
1983
- 1983-09-13 JP JP16765983A patent/JPS5970678A/ja active Granted
- 1983-09-14 BE BE0/211528A patent/BE897750A/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5970678A (ja) | 1984-04-21 |
| JPH0520431B2 (enrdf_load_stackoverflow) | 1993-03-19 |
| DE3234531C2 (enrdf_load_stackoverflow) | 1991-07-04 |
| DE3234531A1 (de) | 1984-03-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RE | Patent lapsed |
Owner name: BAYER A.G. Effective date: 19950930 |