JPS6241668B2 - - Google Patents
Info
- Publication number
- JPS6241668B2 JPS6241668B2 JP57160916A JP16091682A JPS6241668B2 JP S6241668 B2 JPS6241668 B2 JP S6241668B2 JP 57160916 A JP57160916 A JP 57160916A JP 16091682 A JP16091682 A JP 16091682A JP S6241668 B2 JPS6241668 B2 JP S6241668B2
- Authority
- JP
- Japan
- Prior art keywords
- thiadiazole
- mercapto
- general formula
- crystals
- sodium
- 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
- KZXIQMSWVSTGQX-UHFFFAOYSA-N SC1=CN=NS1 Chemical class SC1=CN=NS1 KZXIQMSWVSTGQX-UHFFFAOYSA-N 0.000 claims description 9
- 150000007857 hydrazones Chemical class 0.000 claims description 6
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
- 239000013078 crystal Substances 0.000 description 13
- 239000000203 mixture Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 238000001816 cooling Methods 0.000 description 9
- 229910052979 sodium sulfide Inorganic materials 0.000 description 9
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- VONKGJLSJWJWGY-UHFFFAOYSA-N 4-methyl-n-(2,2,2-trichloroethylideneamino)benzenesulfonamide Chemical compound CC1=CC=C(S(=O)(=O)NN=CC(Cl)(Cl)Cl)C=C1 VONKGJLSJWJWGY-UHFFFAOYSA-N 0.000 description 5
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 5
- 229940073608 benzyl chloride Drugs 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical group 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- FQTIYMRSUOADDK-UHFFFAOYSA-N ethyl 3-bromopropanoate Chemical group CCOC(=O)CCBr FQTIYMRSUOADDK-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- KFZUDNZQQCWGKF-UHFFFAOYSA-M sodium;4-methylbenzenesulfinate Chemical compound [Na+].CC1=CC=C(S([O-])=O)C=C1 KFZUDNZQQCWGKF-UHFFFAOYSA-M 0.000 description 3
- QFCSRTHGBBTPLC-UHFFFAOYSA-N 2h-thiadiazole-5-thione Chemical compound S=C1C=NNS1 QFCSRTHGBBTPLC-UHFFFAOYSA-N 0.000 description 2
- POVCGNAHSFQICQ-UHFFFAOYSA-N 5-benzylsulfanylthiadiazole Chemical compound C=1C=CC=CC=1CSC1=CN=NS1 POVCGNAHSFQICQ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical group BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 2
- OHCLHQCVALHTDN-UHFFFAOYSA-N 1-benzylsulfonyl-4-methylbenzene Chemical compound C1=CC(C)=CC=C1S(=O)(=O)CC1=CC=CC=C1 OHCLHQCVALHTDN-UHFFFAOYSA-N 0.000 description 1
- TXMFDSUMJLQLGB-UHFFFAOYSA-N 1-ethylsulfanyl-4-methylbenzene Chemical compound CCSC1=CC=C(C)C=C1 TXMFDSUMJLQLGB-UHFFFAOYSA-N 0.000 description 1
- YTGSYRVSBPFKMQ-UHFFFAOYSA-N 2,2,2-tribromoacetaldehyde Chemical group BrC(Br)(Br)C=O YTGSYRVSBPFKMQ-UHFFFAOYSA-N 0.000 description 1
- FXJVNINSOKCNJP-UHFFFAOYSA-M 4-methylbenzenesulfinate Chemical compound CC1=CC=C(S([O-])=O)C=C1 FXJVNINSOKCNJP-UHFFFAOYSA-M 0.000 description 1
- HOMSOWZTBJWNHP-UHFFFAOYSA-N 5-chlorothiadiazole Chemical compound ClC1=CN=NS1 HOMSOWZTBJWNHP-UHFFFAOYSA-N 0.000 description 1
- HRKBVAJMGSRDAB-UHFFFAOYSA-N 5-ethylsulfanylthiadiazole Chemical compound CCSC1=CN=NS1 HRKBVAJMGSRDAB-UHFFFAOYSA-N 0.000 description 1
- -1 5-mercapto-1,2,3-thiadiazole anion Chemical class 0.000 description 1
- 229930186147 Cephalosporin Natural products 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- RDHPKYGYEGBMSE-VQEHIDDOSA-N bromoethane Chemical group C[13CH2]Br RDHPKYGYEGBMSE-VQEHIDDOSA-N 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical class [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- AIVORJKUXZAUCG-UHFFFAOYSA-N n-(2,2,2-trichloroethylideneamino)benzenesulfonamide Chemical compound ClC(Cl)(Cl)C=NNS(=O)(=O)C1=CC=CC=C1 AIVORJKUXZAUCG-UHFFFAOYSA-N 0.000 description 1
- SYOSCCXSTYDRGI-UHFFFAOYSA-N n-(2,2-dichloroethenylimino)-4-methylbenzenesulfonamide Chemical compound CC1=CC=C(S(=O)(=O)N=NC=C(Cl)Cl)C=C1 SYOSCCXSTYDRGI-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- ZOCLAPYLSUCOGI-UHFFFAOYSA-M potassium hydrosulfide Chemical compound [SH-].[K+] ZOCLAPYLSUCOGI-UHFFFAOYSA-M 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- DPLVEEXVKBWGHE-UHFFFAOYSA-N potassium sulfide Chemical compound [S-2].[K+].[K+] DPLVEEXVKBWGHE-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- OIIWPAYIXDCDNL-HGFPCDIYSA-M sodium;2,2,3,3-tetradeuterio-3-trimethylsilylpropanoate Chemical compound [Na+].[O-]C(=O)C([2H])([2H])C([2H])([2H])[Si](C)(C)C OIIWPAYIXDCDNL-HGFPCDIYSA-M 0.000 description 1
- 239000010421 standard material Substances 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229940029273 trichloroacetaldehyde Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure 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
- C07D285/06—1,2,3-Thiadiazoles; Hydrogenated 1,2,3-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
- C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57160916A JPS5951271A (ja) | 1982-09-17 | 1982-09-17 | ５−メルカプト−１，２，３−チアジアゾ−ル塩の製造方法 |
| DE8383109037T DE3369985D1 (en) | 1982-09-17 | 1983-09-13 | Method for preparing 1,2,3-trihetero 5-membered heterocyclic compounds |
| DE1983109037 DE103840T1 (de) | 1982-09-17 | 1983-09-13 | Verfahren zur herstellung von 1,2,3-trihetero-5-gliedrigen heterozyklischen verbindungen. |
| EP83109037A EP0103840B1 (en) | 1982-09-17 | 1983-09-13 | Method for preparing 1,2,3-trihetero 5-membered heterocyclic compounds |
| US06/532,922 US4540794A (en) | 1982-09-17 | 1983-09-16 | Method for preparing 5-mercapto-1,2,3-thiadiazole salts |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57160916A JPS5951271A (ja) | 1982-09-17 | 1982-09-17 | ５−メルカプト−１，２，３−チアジアゾ−ル塩の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5951271A JPS5951271A (ja) | 1984-03-24 |
| JPS6241668B2 true JPS6241668B2 (OSRAM) | 1987-09-03 |
Family
ID=15725076
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57160916A Granted JPS5951271A (ja) | 1982-09-17 | 1982-09-17 | ５−メルカプト−１，２，３−チアジアゾ−ル塩の製造方法 |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US4540794A (OSRAM) |
| JP (1) | JPS5951271A (OSRAM) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5995282A (ja) * | 1982-11-22 | 1984-06-01 | Ube Ind Ltd | ５−メルカプト−１，２，３−チアジアゾ−ル塩の製法 |
| JPS6019776A (ja) * | 1983-07-12 | 1985-01-31 | Ube Ind Ltd | 安定化された５―メルカプト―１，２，３―チアジアゾール類組成物 |
| JPS6183177A (ja) * | 1984-09-28 | 1986-04-26 | Ube Ind Ltd | ５−メルカプト−１，２，３−チアジアゾ−ル塩の製法 |
| CN105330613A (zh) * | 2015-11-20 | 2016-02-17 | 哈尔滨工业大学（威海） | 一类氧杂噻二唑-2-氧化物类化合物及其制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4454336A (en) * | 1982-09-27 | 1984-06-12 | American Cyanamid Company | Derivatives of 3-(formylmethylthio)-propanoate |
-
1982
- 1982-09-17 JP JP57160916A patent/JPS5951271A/ja active Granted
-
1983
- 1983-09-16 US US06/532,922 patent/US4540794A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5951271A (ja) | 1984-03-24 |
| US4540794A (en) | 1985-09-10 |
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