DE1670196C3 - Verfahren zur Herstellung von 1,2-Benzisothiazolen - Google Patents
Verfahren zur Herstellung von 1,2-BenzisothiazolenInfo
- Publication number
- DE1670196C3 DE1670196C3 DE19671670196 DE1670196A DE1670196C3 DE 1670196 C3 DE1670196 C3 DE 1670196C3 DE 19671670196 DE19671670196 DE 19671670196 DE 1670196 A DE1670196 A DE 1670196A DE 1670196 C3 DE1670196 C3 DE 1670196C3
- Authority
- DE
- Germany
- Prior art keywords
- parts
- ammonia
- benzisothiazoles
- benzene
- preparation
- 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
Links
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical class C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 title description 6
- 238000000034 method Methods 0.000 title description 6
- 238000002360 preparation method Methods 0.000 title description 2
- 150000003557 thiazoles Chemical class 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 30
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- 229910021529 ammonia Inorganic materials 0.000 description 15
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- CQCOWEWBIGUOSW-UHFFFAOYSA-N Cl.ClC1=CC=CC(=C1)Cl Chemical compound Cl.ClC1=CC=CC(=C1)Cl CQCOWEWBIGUOSW-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- -1 o-mercapto-phenylcarbonyl compounds Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910052715 tantalum Inorganic materials 0.000 description 2
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 2
- VVIXDPOFXLSGIU-UHFFFAOYSA-N 4,5-dichloro-1,2-benzothiazole Chemical compound ClC1=CC=C2SN=CC2=C1Cl VVIXDPOFXLSGIU-UHFFFAOYSA-N 0.000 description 1
- RQYJQKWZHHCWGP-UHFFFAOYSA-N 4,7-dichloro-1,2-benzothiazole Chemical compound ClC1=CC=C(Cl)C2=C1C=NS2 RQYJQKWZHHCWGP-UHFFFAOYSA-N 0.000 description 1
- DHLIRMWNYRKKPN-UHFFFAOYSA-N 4-chloro-1,2-benzothiazole Chemical compound ClC1=CC=CC2=C1C=NS2 DHLIRMWNYRKKPN-UHFFFAOYSA-N 0.000 description 1
- AUYJMVMBVRSCMW-UHFFFAOYSA-N 5-nitro-1,2-benzothiazole Chemical compound [O-][N+](=O)C1=CC=C2SN=CC2=C1 AUYJMVMBVRSCMW-UHFFFAOYSA-N 0.000 description 1
- 241001463143 Auca Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81175A US3682941A (en) | 1967-03-18 | 1970-10-15 | Production of 1,2-benzoisothiazoles |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB0091671 | 1967-03-18 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1670196A1 DE1670196A1 (de) | 1971-01-21 |
| DE1670196B2 DE1670196B2 (de) | 1975-01-30 |
| DE1670196C3 true DE1670196C3 (de) | 1975-09-18 |
Family
ID=6985974
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671670196 Expired DE1670196C3 (de) | 1967-03-18 | 1967-03-18 | Verfahren zur Herstellung von 1,2-Benzisothiazolen |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE712335A (enExample) |
| CH (1) | CH484932A (enExample) |
| DE (1) | DE1670196C3 (enExample) |
| FR (1) | FR1558071A (enExample) |
| GB (1) | GB1208678A (enExample) |
| IT (1) | IT985501B (enExample) |
| NL (1) | NL151992B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2503699C2 (de) * | 1975-01-30 | 1983-04-21 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von 1,2- Benzisothiazolen |
| DE3018108A1 (de) | 1980-05-12 | 1981-11-19 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von 1,2-benzisothhiazolen |
-
1967
- 1967-03-18 DE DE19671670196 patent/DE1670196C3/de not_active Expired
-
1968
- 1968-03-12 CH CH361168A patent/CH484932A/de not_active IP Right Cessation
- 1968-03-14 FR FR1558071D patent/FR1558071A/fr not_active Expired
- 1968-03-14 NL NL6803650A patent/NL151992B/xx not_active IP Right Cessation
- 1968-03-14 GB GB1232468A patent/GB1208678A/en not_active Expired
- 1968-03-16 IT IT3561868A patent/IT985501B/it active
- 1968-03-18 BE BE712335D patent/BE712335A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR1558071A (enExample) | 1969-02-21 |
| NL151992B (nl) | 1977-01-17 |
| NL6803650A (enExample) | 1968-09-19 |
| DE1670196B2 (de) | 1975-01-30 |
| CH484932A (de) | 1970-01-31 |
| DE1670196A1 (de) | 1971-01-21 |
| BE712335A (enExample) | 1968-09-18 |
| IT985501B (it) | 1974-12-10 |
| GB1208678A (en) | 1970-10-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 |