SU588918A3 - Способ получени 2-замещенных1,3,4-тиадиазол-5-тиолов - Google Patents
Способ получени 2-замещенных1,3,4-тиадиазол-5-тиоловInfo
- Publication number
- SU588918A3 SU588918A3 SU731954854A SU1954854A SU588918A3 SU 588918 A3 SU588918 A3 SU 588918A3 SU 731954854 A SU731954854 A SU 731954854A SU 1954854 A SU1954854 A SU 1954854A SU 588918 A3 SU588918 A3 SU 588918A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- reaction mixture
- added
- thiol
- mixture
- carbon disulfide
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 18
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 21
- 239000011541 reaction mixture Substances 0.000 claims description 20
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 12
- -1 3,6-disubstituted tetrazine Chemical class 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 7
- FPVUWZFFEGYCGB-UHFFFAOYSA-N 5-methyl-3h-1,3,4-thiadiazole-2-thione Chemical compound CC1=NN=C(S)S1 FPVUWZFFEGYCGB-UHFFFAOYSA-N 0.000 claims description 6
- 239000012442 inert solvent Substances 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- ZTLMHGOWADYAHM-UHFFFAOYSA-N 5-phenyl-3h-1,3,4-thiadiazole-2-thione Chemical compound S1C(S)=NN=C1C1=CC=CC=C1 ZTLMHGOWADYAHM-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 18
- 239000000047 product Substances 0.000 claims 12
- 239000000203 mixture Substances 0.000 claims 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 10
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 8
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims 8
- 239000002585 base Substances 0.000 claims 6
- 230000020477 pH reduction Effects 0.000 claims 5
- YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 claims 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 5
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims 4
- 239000000243 solution Substances 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 239000008367 deionised water Substances 0.000 claims 3
- 229910021641 deionized water Inorganic materials 0.000 claims 3
- 238000001914 filtration Methods 0.000 claims 3
- 239000007789 gas Substances 0.000 claims 3
- 239000007858 starting material Substances 0.000 claims 3
- DGSFZGQIUBBSDK-UHFFFAOYSA-N 2,3-dihydrothiadiazole-5-thiol Chemical compound C1(=CNNS1)S DGSFZGQIUBBSDK-UHFFFAOYSA-N 0.000 claims 2
- 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 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- 239000006227 byproduct Substances 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 239000012065 filter cake Substances 0.000 claims 2
- 239000012535 impurity Substances 0.000 claims 2
- 229910052708 sodium Inorganic materials 0.000 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 2
- 150000003556 thioamides Chemical class 0.000 claims 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims 1
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims 1
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 claims 1
- CARFETJZUQORNQ-UHFFFAOYSA-N 1h-pyrrole-2-thiol Chemical class SC1=CC=CN1 CARFETJZUQORNQ-UHFFFAOYSA-N 0.000 claims 1
- FJZJUSOFGBXHCV-UHFFFAOYSA-N 2,2-dimethylpropanethioamide Chemical compound CC(C)(C)C(N)=S FJZJUSOFGBXHCV-UHFFFAOYSA-N 0.000 claims 1
- NPCLRBQYESMUPD-UHFFFAOYSA-N 2-methylpropanethioamide Chemical compound CC(C)C(N)=S NPCLRBQYESMUPD-UHFFFAOYSA-N 0.000 claims 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims 1
- JLAMDELLBBZOOX-UHFFFAOYSA-N 3h-1,3,4-thiadiazole-2-thione Chemical compound SC1=NN=CS1 JLAMDELLBBZOOX-UHFFFAOYSA-N 0.000 claims 1
- KKZAOQAHLBXTLJ-UHFFFAOYSA-N 5-benzyl-3h-1,3,4-thiadiazole-2-thione Chemical compound S1C(=S)NN=C1CC1=CC=CC=C1 KKZAOQAHLBXTLJ-UHFFFAOYSA-N 0.000 claims 1
- AIZIJSLXZMNAGM-UHFFFAOYSA-N 5-cyclohexyl-3h-1,3,4-thiadiazole-2-thione Chemical compound S1C(=S)NN=C1C1CCCCC1 AIZIJSLXZMNAGM-UHFFFAOYSA-N 0.000 claims 1
- UFSCJPPXRHCNLK-UHFFFAOYSA-N 5-ethyl-3h-1,3,4-thiadiazole-2-thione Chemical compound CCC1=NN=C(S)S1 UFSCJPPXRHCNLK-UHFFFAOYSA-N 0.000 claims 1
- CJMUOXLDOLNLKB-UHFFFAOYSA-N 5-propan-2-yl-3h-1,3,4-thiadiazole-2-thione Chemical compound CC(C)C1=NNC(=S)S1 CJMUOXLDOLNLKB-UHFFFAOYSA-N 0.000 claims 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- QIOZLISABUUKJY-UHFFFAOYSA-N Thiobenzamide Chemical compound NC(=S)C1=CC=CC=C1 QIOZLISABUUKJY-UHFFFAOYSA-N 0.000 claims 1
- 238000010521 absorption reaction Methods 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 230000009286 beneficial effect Effects 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- WPLXTOVHRYJKSG-UHFFFAOYSA-N butanethioamide Chemical compound CCCC(N)=S WPLXTOVHRYJKSG-UHFFFAOYSA-N 0.000 claims 1
- 239000003610 charcoal Substances 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 238000004090 dissolution Methods 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 238000004445 quantitative analysis Methods 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 235000012976 tarts Nutrition 0.000 claims 1
- 150000004867 thiadiazoles Chemical class 0.000 claims 1
- 238000004448 titration Methods 0.000 claims 1
- 231100000167 toxic agent Toxicity 0.000 claims 1
- 239000003440 toxic substance Substances 0.000 claims 1
- NSMKWTGDPQHTDH-UHFFFAOYSA-N 2-bromo-5-methyl-1,3,4-thiadiazole Chemical compound CC1=NN=C(Br)S1 NSMKWTGDPQHTDH-UHFFFAOYSA-N 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- SQUPFOKOYWHVIT-UHFFFAOYSA-N 2-phenylethanethiohydrazide Chemical compound NNC(=S)CC1=CC=CC=C1 SQUPFOKOYWHVIT-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- HMPUHXCGUHDVBI-UHFFFAOYSA-N 5-methyl-1,3,4-thiadiazol-2-amine Chemical compound CC1=NN=C(N)S1 HMPUHXCGUHDVBI-UHFFFAOYSA-N 0.000 description 1
- 229930186147 Cephalosporin Natural products 0.000 description 1
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- PNALOBAQBMAHBZ-UHFFFAOYSA-N benzenecarbothiohydrazide Chemical compound NNC(=S)C1=CC=CC=C1 PNALOBAQBMAHBZ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical compound [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical class O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/433—Thidiazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00285972A US3824246A (en) | 1972-09-05 | 1972-09-05 | Process for the preparation of 2-substituted-1,3,4-thiadiazole-5-thiols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU588918A3 true SU588918A3 (ru) | 1978-01-15 |
Family
ID=23096476
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU731954854A SU588918A3 (ru) | 1972-09-05 | 1973-09-04 | Способ получени 2-замещенных1,3,4-тиадиазол-5-тиолов |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US3824246A (enExample) |
| KR (1) | KR780000093B1 (enExample) |
| AT (1) | AT326650B (enExample) |
| BE (1) | BE804264A (enExample) |
| CA (1) | CA998677A (enExample) |
| CS (1) | CS168044B2 (enExample) |
| DK (1) | DK134755B (enExample) |
| ES (1) | ES418482A1 (enExample) |
| GB (1) | GB1435346A (enExample) |
| HU (1) | HU166845B (enExample) |
| IE (1) | IE38080B1 (enExample) |
| IL (1) | IL43016A (enExample) |
| PH (1) | PH11086A (enExample) |
| PL (1) | PL86902B1 (enExample) |
| SE (1) | SE387636B (enExample) |
| SU (1) | SU588918A3 (enExample) |
| ZA (1) | ZA735563B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4185417A (en) * | 1978-09-05 | 1980-01-29 | General Products Company, Inc. | Weather seal apparatus |
| CN102219758B (zh) * | 2011-08-01 | 2012-06-27 | 山东济宁裕鑫精细材料有限公司 | 一种2-甲基-5-巯基-1,3,4-噻二唑的合成方法 |
-
1972
- 1972-09-05 US US00285972A patent/US3824246A/en not_active Expired - Lifetime
-
1973
- 1973-08-14 CA CA178,761A patent/CA998677A/en not_active Expired
- 1973-08-14 ZA ZA00735563A patent/ZA735563B/xx unknown
- 1973-08-14 IE IE1393/73A patent/IE38080B1/xx unknown
- 1973-08-17 IL IL43016A patent/IL43016A/en unknown
- 1973-08-30 HU HUEI492A patent/HU166845B/hu unknown
- 1973-08-31 BE BE1005327A patent/BE804264A/xx unknown
- 1973-09-03 SE SE7311979A patent/SE387636B/xx unknown
- 1973-09-04 SU SU731954854A patent/SU588918A3/ru active
- 1973-09-04 GB GB4146673A patent/GB1435346A/en not_active Expired
- 1973-09-04 ES ES418482A patent/ES418482A1/es not_active Expired
- 1973-09-04 KR KR7301478A patent/KR780000093B1/ko not_active Expired
- 1973-09-04 DK DK485473AA patent/DK134755B/da unknown
- 1973-09-04 CS CS6159A patent/CS168044B2/cs unknown
- 1973-09-05 PL PL1973165044A patent/PL86902B1/pl unknown
- 1973-09-05 AT AT770773A patent/AT326650B/de not_active IP Right Cessation
-
1977
- 1977-08-24 PH PH14950A patent/PH11086A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE38080B1 (en) | 1977-12-21 |
| AT326650B (de) | 1975-12-29 |
| CS168044B2 (enExample) | 1976-05-28 |
| US3824246A (en) | 1974-07-16 |
| ZA735563B (en) | 1975-04-30 |
| IL43016A (en) | 1977-01-31 |
| SE387636B (sv) | 1976-09-13 |
| GB1435346A (en) | 1976-05-12 |
| PL86902B1 (enExample) | 1976-06-30 |
| PH11086A (en) | 1977-10-25 |
| DK134755C (enExample) | 1977-09-05 |
| KR780000093B1 (en) | 1978-04-08 |
| IE38080L (en) | 1974-03-05 |
| ES418482A1 (es) | 1976-04-01 |
| HU166845B (enExample) | 1975-06-28 |
| DK134755B (da) | 1977-01-10 |
| BE804264A (fr) | 1974-02-28 |
| CA998677A (en) | 1976-10-19 |
| ATA770773A (de) | 1975-03-15 |
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