DE2152329A1 - Thiocyanatobenzothiazole - Google Patents
ThiocyanatobenzothiazoleInfo
- Publication number
- DE2152329A1 DE2152329A1 DE19712152329 DE2152329A DE2152329A1 DE 2152329 A1 DE2152329 A1 DE 2152329A1 DE 19712152329 DE19712152329 DE 19712152329 DE 2152329 A DE2152329 A DE 2152329A DE 2152329 A1 DE2152329 A1 DE 2152329A1
- Authority
- DE
- Germany
- Prior art keywords
- mixture
- mol
- filtered
- bromine
- methanol
- 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.)
- Pending
Links
- XTRNTWFPJIZGBG-UHFFFAOYSA-N 1,3-benzothiazol-2-yl thiocyanate Chemical class C1=CC=C2SC(SC#N)=NC2=C1 XTRNTWFPJIZGBG-UHFFFAOYSA-N 0.000 title claims 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052731 fluorine Chemical group 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 230000002538 fungal effect Effects 0.000 description 4
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- SGUROPONBUWEJZ-UHFFFAOYSA-N (2-amino-6,7-dichloro-1,3-benzothiazol-4-yl) thiocyanate Chemical compound C1=C(Cl)C(Cl)=C2SC(N)=NC2=C1SC#N SGUROPONBUWEJZ-UHFFFAOYSA-N 0.000 description 1
- VCWIGPSNHDYZHG-UHFFFAOYSA-N (2-amino-6-chloro-1,3-benzothiazol-4-yl) thiocyanate Chemical compound C1=C(Cl)C=C2SC(N)=NC2=C1SC#N VCWIGPSNHDYZHG-UHFFFAOYSA-N 0.000 description 1
- -1 2-amino-6-methylthio-4-thiocyanatobenzothiazole Chemical compound 0.000 description 1
- SDYWXFYBZPNOFX-UHFFFAOYSA-N 3,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C(Cl)=C1 SDYWXFYBZPNOFX-UHFFFAOYSA-N 0.000 description 1
- YSEMCVGMNUUNRK-UHFFFAOYSA-N 3-chloro-4-fluoroaniline Chemical compound NC1=CC=C(F)C(Cl)=C1 YSEMCVGMNUUNRK-UHFFFAOYSA-N 0.000 description 1
- YKFROQCFVXOUPW-UHFFFAOYSA-N 4-(methylthio) aniline Chemical compound CSC1=CC=C(N)C=C1 YKFROQCFVXOUPW-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241000893980 Microsporum canis Species 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000001408 fungistatic effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000006916 nutrient agar Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000126 substance Substances 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
- C07D277/82—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8322070A | 1970-10-22 | 1970-10-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2152329A1 true DE2152329A1 (de) | 1972-04-27 |
Family
ID=22176944
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712152329 Pending DE2152329A1 (de) | 1970-10-22 | 1971-10-20 | Thiocyanatobenzothiazole |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3696114A (enExample) |
| BE (1) | BE774230A (enExample) |
| CH (1) | CH555851A (enExample) |
| DE (1) | DE2152329A1 (enExample) |
| FR (1) | FR2113087A5 (enExample) |
| GB (1) | GB1324300A (enExample) |
| IL (1) | IL37932A (enExample) |
| NL (1) | NL7114421A (enExample) |
| SE (1) | SE372017B (enExample) |
| ZA (1) | ZA716821B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4381394A (en) * | 1982-03-29 | 1983-04-26 | Norwich Eaton Pharmaceuticals, Inc. | 6,7-Dichloro-2-[(methyl-2-pyrrolidylidene)amino]-4-thiocyanatobenzothiazole |
-
1970
- 1970-10-22 US US83220A patent/US3696114A/en not_active Expired - Lifetime
-
1971
- 1971-10-12 ZA ZA716821A patent/ZA716821B/xx unknown
- 1971-10-14 IL IL37932A patent/IL37932A/xx unknown
- 1971-10-18 SE SE7113144A patent/SE372017B/xx unknown
- 1971-10-20 BE BE774230A patent/BE774230A/xx unknown
- 1971-10-20 DE DE19712152329 patent/DE2152329A1/de active Pending
- 1971-10-20 NL NL7114421A patent/NL7114421A/xx unknown
- 1971-10-21 FR FR7137926A patent/FR2113087A5/fr not_active Expired
- 1971-10-21 CH CH1533571A patent/CH555851A/xx not_active IP Right Cessation
- 1971-10-22 GB GB4912371A patent/GB1324300A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4381394A (en) * | 1982-03-29 | 1983-04-26 | Norwich Eaton Pharmaceuticals, Inc. | 6,7-Dichloro-2-[(methyl-2-pyrrolidylidene)amino]-4-thiocyanatobenzothiazole |
Also Published As
| Publication number | Publication date |
|---|---|
| IL37932A0 (en) | 1971-12-29 |
| AU3487171A (en) | 1973-05-03 |
| GB1324300A (en) | 1973-07-25 |
| SE372017B (enExample) | 1974-12-09 |
| ZA716821B (en) | 1973-05-30 |
| CH555851A (de) | 1974-11-15 |
| IL37932A (en) | 1974-09-10 |
| US3696114A (en) | 1972-10-03 |
| BE774230A (fr) | 1972-04-20 |
| FR2113087A5 (enExample) | 1972-06-23 |
| NL7114421A (enExample) | 1972-04-25 |
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