DE1960981A1 - Verfahren zur Herstellung eines 3-Amino-5-mercapto-1,2,4-triazols - Google Patents
Verfahren zur Herstellung eines 3-Amino-5-mercapto-1,2,4-triazolsInfo
- Publication number
- DE1960981A1 DE1960981A1 DE19691960981 DE1960981A DE1960981A1 DE 1960981 A1 DE1960981 A1 DE 1960981A1 DE 19691960981 DE19691960981 DE 19691960981 DE 1960981 A DE1960981 A DE 1960981A DE 1960981 A1 DE1960981 A1 DE 1960981A1
- Authority
- DE
- Germany
- Prior art keywords
- triazole
- solution
- carbon disulfide
- aqueous base
- preparation
- 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
- 238000000034 method Methods 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title claims description 10
- WZUUZPAYWFIBDF-UHFFFAOYSA-N 5-amino-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound NC1=NNC(S)=N1 WZUUZPAYWFIBDF-UHFFFAOYSA-N 0.000 title claims description 8
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 10
- 150000003852 triazoles Chemical class 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical compound NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 claims description 2
- -1 iriethylamine Chemical compound 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 235000011056 potassium acetate Nutrition 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 9
- 239000002585 base Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- OTXHZHQQWQTQMW-UHFFFAOYSA-N (diaminomethylideneamino)azanium;hydrogen carbonate Chemical compound OC([O-])=O.N[NH2+]C(N)=N OTXHZHQQWQTQMW-UHFFFAOYSA-N 0.000 description 1
- FZJMSTZGWFCPCX-UHFFFAOYSA-N 1-iminoguanidine Chemical compound NC(=N)N=N FZJMSTZGWFCPCX-UHFFFAOYSA-N 0.000 description 1
- 244000228957 Ferula foetida Species 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
Classifications
-
- 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
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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 to ring carbon atoms
- C07D249/14—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5789168 | 1968-12-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1960981A1 true DE1960981A1 (de) | 1970-06-25 |
Family
ID=10480295
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691960981 Pending DE1960981A1 (de) | 1968-12-05 | 1969-12-04 | Verfahren zur Herstellung eines 3-Amino-5-mercapto-1,2,4-triazols |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE742748A (ja) |
| DE (1) | DE1960981A1 (ja) |
| GB (1) | GB1232838A (ja) |
| NL (1) | NL6918066A (ja) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5559243A (en) * | 1994-12-13 | 1996-09-24 | Nippon Carbide Kogyo Kabushiki Kaisha | Processes for producing a salt of N-guanidino thiourea and 3-amino-5-mercapto-1,2,4-triazole |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA943337B (en) * | 1993-05-18 | 1995-01-27 | Buckman Labor Inc | The reaction of a metal salt of an s-substituted n-cyanodi-thioiminocarbonate with hydrazine or hydrazine hydrate |
| US5606091A (en) * | 1993-05-18 | 1997-02-25 | Buckman Laboratories International, Inc. | Preparation of symmetrical or unsymmetrical disubstituted n-cyanodithioiminocarbonates |
-
1968
- 1968-12-05 GB GB1232838D patent/GB1232838A/en not_active Expired
-
1969
- 1969-12-02 NL NL6918066A patent/NL6918066A/xx unknown
- 1969-12-04 DE DE19691960981 patent/DE1960981A1/de active Pending
- 1969-12-05 BE BE742748D patent/BE742748A/xx unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5559243A (en) * | 1994-12-13 | 1996-09-24 | Nippon Carbide Kogyo Kabushiki Kaisha | Processes for producing a salt of N-guanidino thiourea and 3-amino-5-mercapto-1,2,4-triazole |
| US5714617A (en) * | 1994-12-13 | 1998-02-03 | Nippon Carbide Kogyo Kabushiki Kaisha | Processes for producing a salt of N-guanidino thiourea and 3-amino-5-mercapto-1,2,4-triazole |
Also Published As
| Publication number | Publication date |
|---|---|
| BE742748A (ja) | 1970-05-14 |
| GB1232838A (ja) | 1971-05-19 |
| NL6918066A (ja) | 1970-06-09 |
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