JPH0520431B2 - - Google Patents
Info
- Publication number
- JPH0520431B2 JPH0520431B2 JP16765983A JP16765983A JPH0520431B2 JP H0520431 B2 JPH0520431 B2 JP H0520431B2 JP 16765983 A JP16765983 A JP 16765983A JP 16765983 A JP16765983 A JP 16765983A JP H0520431 B2 JPH0520431 B2 JP H0520431B2
- Authority
- JP
- Japan
- Prior art keywords
- chlorobenzthiazole
- mercaptobenzthiazole
- reaction
- chlorine
- mol
- 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.)
- Expired - Lifetime
Links
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 claims description 25
- BSQLQMLFTHJVKS-UHFFFAOYSA-N 2-chloro-1,3-benzothiazole Chemical compound C1=CC=C2SC(Cl)=NC2=C1 BSQLQMLFTHJVKS-UHFFFAOYSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- WQYSXVGEZYESBR-UHFFFAOYSA-N thiophosphoryl chloride Chemical compound ClP(Cl)(Cl)=S WQYSXVGEZYESBR-UHFFFAOYSA-N 0.000 claims description 8
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 6
- 150000003512 tertiary amines Chemical class 0.000 claims description 5
- 239000006227 byproduct Substances 0.000 claims description 4
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- 238000005660 chlorination reaction Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims 1
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 238000004821 distillation Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229910018894 PSCl3 Inorganic materials 0.000 description 2
- JJWKPURADFRFRB-UHFFFAOYSA-N carbonyl sulfide Chemical compound O=C=S JJWKPURADFRFRB-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 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
- PNEABRNAYDDYJK-UHFFFAOYSA-N 2-hydroxy-n-methyl-n-phenylacetamide Chemical compound OCC(=O)N(C)C1=CC=CC=C1 PNEABRNAYDDYJK-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 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
- 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
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000003756 stirring 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)
- Thiazole And Isothizaole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3234531.3 | 1982-09-17 | ||
| DE19823234531 DE3234531A1 (de) | 1982-09-17 | 1982-09-17 | Verfahren zur herstellung von 2-chlorbenzthiazol aus 2-mercaptobenzthiazol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5970678A JPS5970678A (ja) | 1984-04-21 |
| JPH0520431B2 true JPH0520431B2 (enrdf_load_stackoverflow) | 1993-03-19 |
Family
ID=6173505
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16765983A Granted JPS5970678A (ja) | 1982-09-17 | 1983-09-13 | ２−メルカプトベンズチアゾ−ルからの２−クロロベンズチアゾ−ルの製造方法 |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS5970678A (enrdf_load_stackoverflow) |
| BE (1) | BE897750A (enrdf_load_stackoverflow) |
| DE (1) | DE3234531A1 (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1989000617A1 (en) * | 1987-07-17 | 1989-01-26 | Nobuyuki Koura | Process for preparing superconductor |
Families Citing this family (3)
| 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 |
| 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
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1989000617A1 (en) * | 1987-07-17 | 1989-01-26 | Nobuyuki Koura | Process for preparing superconductor |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5970678A (ja) | 1984-04-21 |
| DE3234531C2 (enrdf_load_stackoverflow) | 1991-07-04 |
| DE3234531A1 (de) | 1984-03-22 |
| BE897750A (fr) | 1984-03-14 |
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