GB497659A - Manufacture of 2-alkyl-tetrahydrobenzselenazoles - Google Patents
Manufacture of 2-alkyl-tetrahydrobenzselenazolesInfo
- Publication number
- GB497659A GB497659A GB17351/37A GB1735137A GB497659A GB 497659 A GB497659 A GB 497659A GB 17351/37 A GB17351/37 A GB 17351/37A GB 1735137 A GB1735137 A GB 1735137A GB 497659 A GB497659 A GB 497659A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cyclohexanone
- alkyl
- thio
- seleno
- chloro
- 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
- 238000004519 manufacturing process Methods 0.000 title 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
- CCHNWURRBFGQCD-UHFFFAOYSA-N 2-chlorocyclohexan-1-one Chemical compound ClC1CCCCC1=O CCHNWURRBFGQCD-UHFFFAOYSA-N 0.000 abstract 3
- 239000000194 fatty acid Substances 0.000 abstract 3
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 abstract 2
- 239000007795 chemical reaction product Substances 0.000 abstract 2
- 229910052711 selenium Chemical group 0.000 abstract 2
- 239000011669 selenium Chemical group 0.000 abstract 2
- FXEIVSYQEOJLBU-UHFFFAOYSA-N 1-$l^{1}-selanylethanimine Chemical compound CC([Se])=N FXEIVSYQEOJLBU-UHFFFAOYSA-N 0.000 abstract 1
- TTZFIQWMTOJEMU-UHFFFAOYSA-N 2-ethyl-2,3,3a,4-tetrahydro-1,3-benzothiazole Chemical compound C(C)C1SC=2C(N1)CC=CC2 TTZFIQWMTOJEMU-UHFFFAOYSA-N 0.000 abstract 1
- KPBQCKBLDFKAEB-UHFFFAOYSA-N 2-methyl-2,3,3a,4-tetrahydro-1,3-benzoselenazole Chemical compound CC1[Se]C=2C(N1)CC=CC=2 KPBQCKBLDFKAEB-UHFFFAOYSA-N 0.000 abstract 1
- XGKVLNBTWHUUFM-UHFFFAOYSA-N 2-methyl-2,3,3a,4-tetrahydro-1,3-benzothiazole Chemical compound CC1SC=2C(N1)CC=CC2 XGKVLNBTWHUUFM-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000008020 evaporation Effects 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- 239000000706 filtrate Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- WPZSAUFQHYFIPG-UHFFFAOYSA-N propanethioamide Chemical compound CCC(N)=S WPZSAUFQHYFIPG-UHFFFAOYSA-N 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 abstract 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Thiazole And Isothizaole Compounds (AREA)
Abstract
2-Alkyl-tetrahydrobenzthiazoles and 2-alkyl-tetrahydrobenzselenazoles are prepared by causing an ortho-halogen-cyclohexanone to react with a thio-fatty acid amide or a seleno-fatty acid amide or a substituted thio- or seleno-fatty acid amide. The compounds have the general formula <FORM:0497659/IV/1> where Y=sulphur or selenium, and R=an alkyl or a substituted alkyl group. The reaction is preferably conducted at a raised temperature. In examples: (1) o-chloro-cyclohexanone and thio-acetamide are heated together, and the reaction product treated with caustic soda, and the oil so liberated extracted with ether. The residue on evaporation of the ether is distilled under reduced pressure to give 2-methyl-tetra-hydro - benzothiazole; (2) o - chloro - cyclohexanone, alcohol and seleno-acetamide are heated together, the reaction product is taken up in water and filtered from the precipitated selenium. Caustic soda is added to the filtrate to precipitate the 2-methyl-tetrahydro-benzselenazole; (3) o-chloro-cyclohexanone and thio-propionamide are heated together and the product treated with caustic soda to give 2-ethyl-tetrahydrobenzothiazole.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE497659X | 1936-07-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB497659A true GB497659A (en) | 1938-12-22 |
Family
ID=6545208
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB17351/37A Expired GB497659A (en) | 1936-07-29 | 1937-06-22 | Manufacture of 2-alkyl-tetrahydrobenzselenazoles |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB497659A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4208420A (en) * | 1977-10-24 | 1980-06-17 | Laboratoires Jacques Logeais | New benzo [d] thiazole derivatives, process for their preparation and their therapeutic applications |
-
1937
- 1937-06-22 GB GB17351/37A patent/GB497659A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4208420A (en) * | 1977-10-24 | 1980-06-17 | Laboratoires Jacques Logeais | New benzo [d] thiazole derivatives, process for their preparation and their therapeutic applications |
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