DE2153590A1 - Thiocyanatobenzothiazole - Google Patents
ThiocyanatobenzothiazoleInfo
- Publication number
- DE2153590A1 DE2153590A1 DE19712153590 DE2153590A DE2153590A1 DE 2153590 A1 DE2153590 A1 DE 2153590A1 DE 19712153590 DE19712153590 DE 19712153590 DE 2153590 A DE2153590 A DE 2153590A DE 2153590 A1 DE2153590 A1 DE 2153590A1
- Authority
- DE
- Germany
- Prior art keywords
- mixture
- ing
- mol
- added
- filtered
- 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 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 28
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 5
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 claims description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 3
- 239000012346 acetyl chloride Substances 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000003851 azoles Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 16
- 239000007787 solid Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- HRXZRAXKKNUKRF-UHFFFAOYSA-N 4-ethylaniline Chemical compound CCC1=CC=C(N)C=C1 HRXZRAXKKNUKRF-UHFFFAOYSA-N 0.000 description 2
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 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
- WAIKDGNQZPPWET-UHFFFAOYSA-N (2-amino-6-ethyl-1,3-benzothiazol-4-yl) thiocyanate Chemical compound CCC1=CC(SC#N)=C2N=C(N)SC2=C1 WAIKDGNQZPPWET-UHFFFAOYSA-N 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
- NYMDPDNETOLVBS-UHFFFAOYSA-N 4-fluoro-3-methylaniline Chemical compound CC1=CC(N)=CC=C1F NYMDPDNETOLVBS-UHFFFAOYSA-N 0.000 description 1
- 101500021173 Aplysia californica Myomodulin-E Proteins 0.000 description 1
- 241000244188 Ascaris suum Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241001464384 Hymenolepis nana Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 208000014837 parasitic helminthiasis infectious disease Diseases 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8495270A | 1970-10-28 | 1970-10-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2153590A1 true DE2153590A1 (de) | 1972-05-04 |
Family
ID=22188237
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712153590 Pending DE2153590A1 (de) | 1970-10-28 | 1971-10-27 | Thiocyanatobenzothiazole |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3706759A (en:Method) |
| AU (1) | AU455235B2 (en:Method) |
| BE (1) | BE774427A (en:Method) |
| CH (1) | CH561193A5 (en:Method) |
| DE (1) | DE2153590A1 (en:Method) |
| FR (1) | FR2111892B1 (en:Method) |
| GB (1) | GB1328079A (en:Method) |
| IL (1) | IL37971A (en:Method) |
| NL (1) | NL7114700A (en:Method) |
| ZA (1) | ZA717018B (en:Method) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4012409A (en) * | 1975-12-29 | 1977-03-15 | Morton-Norwich Products, Inc. | N-(6-Ethyl-4-thiocyanato-2-benzothiazolyl)-5-nitrofuramide |
| US4169093A (en) * | 1978-05-25 | 1979-09-25 | Morton-Norwich Products, Inc. | 2-Amino-5-phenylmethoxy-6-methoxybenzothiazole hydrochloride |
-
1970
- 1970-10-28 US US84952A patent/US3706759A/en not_active Expired - Lifetime
-
1971
- 1971-10-20 IL IL37971A patent/IL37971A/xx unknown
- 1971-10-20 ZA ZA717018A patent/ZA717018B/xx unknown
- 1971-10-22 GB GB4912771A patent/GB1328079A/en not_active Expired
- 1971-10-25 BE BE774427A patent/BE774427A/xx unknown
- 1971-10-26 NL NL7114700A patent/NL7114700A/xx unknown
- 1971-10-27 CH CH1568771A patent/CH561193A5/xx not_active IP Right Cessation
- 1971-10-27 DE DE19712153590 patent/DE2153590A1/de active Pending
- 1971-10-27 AU AU35053/71A patent/AU455235B2/en not_active Expired
- 1971-10-27 FR FR7138643A patent/FR2111892B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ZA717018B (en) | 1973-06-27 |
| IL37971A0 (en) | 1971-12-29 |
| AU455235B2 (en) | 1974-11-21 |
| BE774427A (fr) | 1972-04-25 |
| GB1328079A (en) | 1973-08-30 |
| FR2111892B1 (en:Method) | 1974-10-18 |
| AU3505371A (en) | 1973-05-03 |
| US3706759A (en) | 1972-12-19 |
| CH561193A5 (en:Method) | 1975-04-30 |
| IL37971A (en) | 1974-09-10 |
| NL7114700A (en:Method) | 1972-05-03 |
| FR2111892A1 (en:Method) | 1972-06-09 |
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