DE2106200C3 - Verfahren zur Herstellung von 2-(4-Aminophenyl)-6-methyl-benzothiazol - Google Patents
Verfahren zur Herstellung von 2-(4-Aminophenyl)-6-methyl-benzothiazolInfo
- Publication number
- DE2106200C3 DE2106200C3 DE2106200A DE2106200A DE2106200C3 DE 2106200 C3 DE2106200 C3 DE 2106200C3 DE 2106200 A DE2106200 A DE 2106200A DE 2106200 A DE2106200 A DE 2106200A DE 2106200 C3 DE2106200 C3 DE 2106200C3
- Authority
- DE
- Germany
- Prior art keywords
- toluidine
- sulfur
- reaction
- aminophenyl
- methyl
- 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
- XRTJYEIMLZALBD-UHFFFAOYSA-N 4-(6-methyl-1,3-benzothiazol-2-yl)aniline Chemical compound S1C2=CC(C)=CC=C2N=C1C1=CC=C(N)C=C1 XRTJYEIMLZALBD-UHFFFAOYSA-N 0.000 title claims description 18
- 238000000034 method Methods 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title claims description 4
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 claims description 42
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 15
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 239000011593 sulfur Substances 0.000 claims description 12
- -1 p-toluidine Sulfur Chemical compound 0.000 claims description 2
- 239000012043 crude product Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000004809 thin layer chromatography 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
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
- C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2106200A DE2106200C3 (de) | 1971-02-10 | 1971-02-10 | Verfahren zur Herstellung von 2-(4-Aminophenyl)-6-methyl-benzothiazol |
| NL7200907A NL7200907A (enExample) | 1971-02-10 | 1972-01-21 | |
| IT20263/72A IT954881B (it) | 1971-02-10 | 1972-02-05 | Procedimento per la preparazione di 2 4 amminofenil 6 metil benzotiazolo |
| US00224105A US3801587A (en) | 1971-02-10 | 1972-02-07 | Process for the preparation of 2-(4-aminophenyl)-6-methyl-benzothiazole |
| BR000711/72A BR7200711D0 (pt) | 1971-02-10 | 1972-02-08 | Processo para a fabricacao de 2-(4-aminofenil)-6-metilbenzotiazol |
| ES399603A ES399603A1 (es) | 1971-02-10 | 1972-02-09 | Procedimiento para la obtencion de 2-(4-aminofenil)-6-me- til-benzotiazol. |
| JP1368572A JPS5627513B1 (enExample) | 1971-02-10 | 1972-02-09 | |
| CH182872A CH567492A5 (enExample) | 1971-02-10 | 1972-02-09 | |
| SU1746781A SU424356A3 (ru) | 1971-02-10 | 1972-02-09 | Способ получения 2- |
| PL1972153401A PL88980B1 (enExample) | 1971-02-10 | 1972-02-09 | |
| FR7204294A FR2126810A5 (enExample) | 1971-02-10 | 1972-02-09 | |
| GB606472A GB1335638A (en) | 1971-02-10 | 1972-02-09 | Process for the preparation of 2- 4-amino-phenyl-6-methyl- benzothiazole |
| BE779155A BE779155A (fr) | 1971-02-10 | 1972-02-09 | Preparation d'un aminophenyl-benzothiazole |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2106200A DE2106200C3 (de) | 1971-02-10 | 1971-02-10 | Verfahren zur Herstellung von 2-(4-Aminophenyl)-6-methyl-benzothiazol |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2106200A1 DE2106200A1 (de) | 1972-09-14 |
| DE2106200B2 DE2106200B2 (de) | 1979-07-19 |
| DE2106200C3 true DE2106200C3 (de) | 1980-03-27 |
Family
ID=5798304
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2106200A Expired DE2106200C3 (de) | 1971-02-10 | 1971-02-10 | Verfahren zur Herstellung von 2-(4-Aminophenyl)-6-methyl-benzothiazol |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3801587A (enExample) |
| JP (1) | JPS5627513B1 (enExample) |
| BE (1) | BE779155A (enExample) |
| BR (1) | BR7200711D0 (enExample) |
| CH (1) | CH567492A5 (enExample) |
| DE (1) | DE2106200C3 (enExample) |
| ES (1) | ES399603A1 (enExample) |
| FR (1) | FR2126810A5 (enExample) |
| GB (1) | GB1335638A (enExample) |
| IT (1) | IT954881B (enExample) |
| NL (1) | NL7200907A (enExample) |
| PL (1) | PL88980B1 (enExample) |
| SU (1) | SU424356A3 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE816584A (fr) * | 1973-06-27 | 1974-12-19 | Colorant au soufre et son procede de preparation | |
| DE4225295A1 (de) * | 1992-07-31 | 1994-02-03 | Hoechst Ag | Wasserunlösliche Azofarbmittel |
| DE4227029A1 (de) * | 1992-08-14 | 1994-02-17 | Basf Ag | Verfahren zur Herstellung von 2-(4'-Aminophenyl)-benzthiazolverbindungen |
-
1971
- 1971-02-10 DE DE2106200A patent/DE2106200C3/de not_active Expired
-
1972
- 1972-01-21 NL NL7200907A patent/NL7200907A/xx unknown
- 1972-02-05 IT IT20263/72A patent/IT954881B/it active
- 1972-02-07 US US00224105A patent/US3801587A/en not_active Expired - Lifetime
- 1972-02-08 BR BR000711/72A patent/BR7200711D0/pt unknown
- 1972-02-09 JP JP1368572A patent/JPS5627513B1/ja active Pending
- 1972-02-09 FR FR7204294A patent/FR2126810A5/fr not_active Expired
- 1972-02-09 ES ES399603A patent/ES399603A1/es not_active Expired
- 1972-02-09 PL PL1972153401A patent/PL88980B1/pl unknown
- 1972-02-09 CH CH182872A patent/CH567492A5/xx not_active IP Right Cessation
- 1972-02-09 SU SU1746781A patent/SU424356A3/ru active
- 1972-02-09 GB GB606472A patent/GB1335638A/en not_active Expired
- 1972-02-09 BE BE779155A patent/BE779155A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2126810A5 (enExample) | 1972-10-06 |
| GB1335638A (en) | 1973-10-31 |
| SU424356A3 (ru) | 1974-04-15 |
| DE2106200A1 (de) | 1972-09-14 |
| IT954881B (it) | 1973-09-15 |
| DE2106200B2 (de) | 1979-07-19 |
| BR7200711D0 (pt) | 1973-08-23 |
| JPS5627513B1 (enExample) | 1981-06-25 |
| US3801587A (en) | 1974-04-02 |
| PL88980B1 (enExample) | 1976-10-30 |
| BE779155A (fr) | 1972-08-09 |
| ES399603A1 (es) | 1975-06-01 |
| CH567492A5 (enExample) | 1975-10-15 |
| NL7200907A (enExample) | 1972-08-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| OGA | New person/name/address of the applicant | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |