DE2162324C2 - Verfahren zur Herstellung von 2-Mercapto-1,3,4-thiadiazolen - Google Patents
Verfahren zur Herstellung von 2-Mercapto-1,3,4-thiadiazolenInfo
- Publication number
- DE2162324C2 DE2162324C2 DE2162324A DE2162324A DE2162324C2 DE 2162324 C2 DE2162324 C2 DE 2162324C2 DE 2162324 A DE2162324 A DE 2162324A DE 2162324 A DE2162324 A DE 2162324A DE 2162324 C2 DE2162324 C2 DE 2162324C2
- Authority
- DE
- Germany
- Prior art keywords
- mercapto
- general formula
- preparation
- acid
- thiadiazoles
- 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
- 238000000034 method Methods 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 3
- JLAMDELLBBZOOX-UHFFFAOYSA-N 3h-1,3,4-thiadiazole-2-thione Chemical class SC1=NN=CS1 JLAMDELLBBZOOX-UHFFFAOYSA-N 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- YNNGZCVDIREDDK-UHFFFAOYSA-N aminocarbamodithioic acid Chemical compound NNC(S)=S YNNGZCVDIREDDK-UHFFFAOYSA-N 0.000 claims description 3
- -1 ten-butyl Chemical group 0.000 description 8
- 239000002253 acid Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 150000002905 orthoesters Chemical class 0.000 description 3
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 159000000001 potassium salts Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 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 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
- PYVUFGZVZNBZRY-UHFFFAOYSA-N 5-propyl-3h-1,3,4-thiadiazole-2-thione Chemical compound CCCC1=NNC(=S)S1 PYVUFGZVZNBZRY-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- OUKFYDVOMHUWQD-UHFFFAOYSA-N C(N)(=N)SN1SC(=CN1)C Chemical compound C(N)(=N)SN1SC(=CN1)C OUKFYDVOMHUWQD-UHFFFAOYSA-N 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
- GDERDRPPFIVRBK-UHFFFAOYSA-N N-(5-methyl-3H-thiadiazol-2-yl)acetamide Chemical compound C(C)(=O)NN1SC(=CN1)C GDERDRPPFIVRBK-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- NSIMQTOXNOFWBP-UHFFFAOYSA-N acetamidothiourea Chemical compound CC(=O)NNC(N)=S NSIMQTOXNOFWBP-UHFFFAOYSA-N 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011049 pearl Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000003139 primary aliphatic amines Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003510 tertiary aliphatic amines Chemical class 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12946670 | 1970-12-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2162324A1 DE2162324A1 (de) | 1972-07-20 |
| DE2162324C2 true DE2162324C2 (de) | 1983-09-15 |
Family
ID=15010175
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712167319 Expired DE2167319C2 (de) | 1970-12-30 | 1971-12-15 | Verfahren zur Herstellung von 2-Mercapto-1,3,4-thiadiazolen |
| DE19712167320 Expired DE2167320C2 (de) | 1970-12-30 | 1971-12-15 | Verfahren zur Herstellung von 2-Mercapto-1,3,4-thiadiazolen |
| DE2162324A Expired DE2162324C2 (de) | 1970-12-30 | 1971-12-15 | Verfahren zur Herstellung von 2-Mercapto-1,3,4-thiadiazolen |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712167319 Expired DE2167319C2 (de) | 1970-12-30 | 1971-12-15 | Verfahren zur Herstellung von 2-Mercapto-1,3,4-thiadiazolen |
| DE19712167320 Expired DE2167320C2 (de) | 1970-12-30 | 1971-12-15 | Verfahren zur Herstellung von 2-Mercapto-1,3,4-thiadiazolen |
Country Status (5)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5747672B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1973-10-13 | 1982-10-12 | ||
| FR2951168B1 (fr) | 2009-10-08 | 2012-04-20 | Michelin Soc Tech | Thiadiazole utilisable comme accelerateur de vulcanisation et son procede d'obtention |
| FR2951181B1 (fr) | 2009-10-08 | 2011-10-28 | Michelin Soc Tech | Composition de caoutchouc comprenant un thiadiazole |
| 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 |
| CN114380770B (zh) * | 2021-12-24 | 2022-12-09 | 山东艾孚特科技有限公司 | 利用固体超强酸催化的甲基巯基噻二唑的合成工艺 |
-
1971
- 1971-12-08 US US00206192A patent/US3798229A/en not_active Expired - Lifetime
- 1971-12-15 DE DE19712167319 patent/DE2167319C2/de not_active Expired
- 1971-12-15 DE DE19712167320 patent/DE2167320C2/de not_active Expired
- 1971-12-15 DE DE2162324A patent/DE2162324C2/de not_active Expired
- 1971-12-17 CH CH326475A patent/CH569725A5/xx not_active IP Right Cessation
- 1971-12-17 CH CH1848271A patent/CH563380A5/xx not_active IP Right Cessation
- 1971-12-29 GB GB6058971A patent/GB1382998A/en not_active Expired
- 1971-12-29 FR FR7147384A patent/FR2121103A5/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2167320C2 (de) | 1984-07-05 |
| FR2121103A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-08-18 |
| CH563380A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-06-30 |
| CH569725A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-11-28 |
| DE2162324A1 (de) | 1972-07-20 |
| DE2167319C2 (de) | 1984-07-05 |
| GB1382998A (en) | 1975-02-05 |
| US3798229A (en) | 1974-03-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8172 | Supplementary division/partition in: |
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|
| Q171 | Divided out to: |
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| 8181 | Inventor (new situation) |
Free format text: KARIYONE, KAZUO, KYOTO, JP HARADA, HIROKICHI, NISHINOMIYA, JP KURITA, MASARU, TAKATSUKI, JP UEDA, YUTAKA, TOYONAKA, JP FURUHASHI, TAKAHIRO, FUKUOKA, JP NAKAMURA, HITOSHI, TOYONAKA, JP WATANABE, HIROTOSHI, IKEDA, JP |
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| 8172 | Supplementary division/partition in: |
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| Q171 | Divided out to: |
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| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| AH | Division in |
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