GB737568A - Improvements in or relating to cyclic nitrogen compounds - Google Patents
Improvements in or relating to cyclic nitrogen compoundsInfo
- Publication number
- GB737568A GB737568A GB1473052A GB1473052A GB737568A GB 737568 A GB737568 A GB 737568A GB 1473052 A GB1473052 A GB 1473052A GB 1473052 A GB1473052 A GB 1473052A GB 737568 A GB737568 A GB 737568A
- Authority
- GB
- United Kingdom
- Prior art keywords
- guanidino
- thiadiazole
- mercapto
- triazole
- dithiocarbamic acid
- 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
- -1 cyclic nitrogen compounds Chemical class 0.000 title 1
- 229910017464 nitrogen compound Inorganic materials 0.000 title 1
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 abstract 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 6
- HWSVUOAFEQLJIQ-UHFFFAOYSA-N (diaminomethylideneamino)carbamodithioic acid Chemical compound NC(N)=NNC(S)=S HWSVUOAFEQLJIQ-UHFFFAOYSA-N 0.000 abstract 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- 239000002585 base Substances 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- 150000003852 triazoles Chemical class 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- JVPGHBWKJNZEDB-UHFFFAOYSA-N N-(2H-triazol-4-yl)thiohydroxylamine Chemical compound SNC1=CNN=N1 JVPGHBWKJNZEDB-UHFFFAOYSA-N 0.000 abstract 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical compound NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- 238000002844 melting Methods 0.000 abstract 2
- 230000007935 neutral effect Effects 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 2
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 abstract 2
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 abstract 1
- UBDZFAGVPPMTIT-UHFFFAOYSA-N 2-aminoguanidine;hydron;chloride Chemical compound [Cl-].NC(N)=N[NH3+] UBDZFAGVPPMTIT-UHFFFAOYSA-N 0.000 abstract 1
- GRBBTGGZVUFCRP-UHFFFAOYSA-N 4-amino-1,2-dihydrotriazole-5-thione Chemical compound NC=1NN=NC=1S GRBBTGGZVUFCRP-UHFFFAOYSA-N 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- SZPMEGPTMWLUIS-UHFFFAOYSA-N Nc1nnsc1S Chemical compound Nc1nnsc1S SZPMEGPTMWLUIS-UHFFFAOYSA-N 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 150000004703 alkoxides Chemical class 0.000 abstract 1
- 239000012736 aqueous medium Substances 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 abstract 1
- 239000000356 contaminant Substances 0.000 abstract 1
- 238000002425 crystallisation Methods 0.000 abstract 1
- 230000008025 crystallization Effects 0.000 abstract 1
- 238000000605 extraction Methods 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 230000008018 melting Effects 0.000 abstract 1
- 230000004048 modification Effects 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
- 230000020477 pH reduction Effects 0.000 abstract 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
- C07D285/135—Nitrogen atoms
-
- 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
Abstract
3 - Amino - 5 - mercapto - 1 : 2 : 4 - triazole, 2 - mercapto - 5 - amino - 1 : 3 : 4 - thiadiazole or mixtures thereof are prepared by subjecting guanidino dithiocarbamic acid to heat treatment in neutral or alkaline condition, preferably in aqueous medium. At temperatures below 100 DEG C. and under neutral or slightly alkaline conditions the product is chiefly the thiadiazole, whilst high temperatures and pH values favour the triazole formation. A high-melting contaminant of formula C3H6N6S2 is often obtained and the mixture is resolved by extraction of the thiadiazole with ethanol, followed by crystallization of residue from water and then dilute hydrochloric acid to yield the pure triazole. A modification of the invention consists of preparing the required guanidino dithiocarbamic acid in situ from aminoguanidine and carbon disulphide thereafter cyclizing by addition of a strong base preferably in water; or alternatively preparing the triazole directly from aminoguanidine and carbon disulphide by heating with a strong base under substantially anhydrous conditions. Specified bases are alkali metal hydroxides, carbonates and alkoxides and triethylamine (preferably used in alcohol). In examples (1) guanidino dithiocarbamic acid inner salt is treated with either water or caustic soda solution, using varying reaction periods and temperatures, thereby obtaining on acidification either mercapto amino thiadiazole, mercaptoaminotriazole or mixtures of these together with a high melting residue; (2) guanidino dithiocarbamic acid inner salt is heated alone to produce mercapto aminotriazole; (3) aminoguanidine hydrochloride (or bicarbonate) and carbon disulphide in the presence of sodium methoxide, triethylamine or sodium hydroxide yields mercaptoaminotriazole. Specifications 583,648, [Group XX], 648,185 and 737,567 are referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1473052A GB737568A (en) | 1952-06-11 | 1952-06-11 | Improvements in or relating to cyclic nitrogen compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1473052A GB737568A (en) | 1952-06-11 | 1952-06-11 | Improvements in or relating to cyclic nitrogen compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB737568A true GB737568A (en) | 1955-09-28 |
Family
ID=10046466
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1473052A Expired GB737568A (en) | 1952-06-11 | 1952-06-11 | Improvements in or relating to cyclic nitrogen compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB737568A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1222068B (en) * | 1960-08-16 | 1966-08-04 | Roger Bellon Fa Lab | Process for the preparation of trisubstituted 1, 2, 4-triazoles |
| EP0318096A1 (en) * | 1987-11-23 | 1989-05-31 | DowElanco | Process for the preparation of 3-mercapto-5-amino-(1H)-1,2,4-triazole |
| WO1994026724A2 (en) * | 1993-05-18 | 1994-11-24 | Buckman Laboratories International, Inc. | Preparation of n-cyanodithioimino-carbonates and 3-mercapto-5-amino-1h-1,2,4-triazole |
| RU2747082C2 (en) * | 2016-02-24 | 2021-04-26 | Доринг Интернэшнл Гмбх | Method of production of anti-viral drug |
-
1952
- 1952-06-11 GB GB1473052A patent/GB737568A/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1222068B (en) * | 1960-08-16 | 1966-08-04 | Roger Bellon Fa Lab | Process for the preparation of trisubstituted 1, 2, 4-triazoles |
| EP0318096A1 (en) * | 1987-11-23 | 1989-05-31 | DowElanco | Process for the preparation of 3-mercapto-5-amino-(1H)-1,2,4-triazole |
| AU609904B2 (en) * | 1987-11-23 | 1991-05-09 | Dow Chemical Company, The | Process for the preparation of 3-mercapto-5-amino-(1h)-1,2,4-triazole |
| WO1994026724A2 (en) * | 1993-05-18 | 1994-11-24 | Buckman Laboratories International, Inc. | Preparation of n-cyanodithioimino-carbonates and 3-mercapto-5-amino-1h-1,2,4-triazole |
| WO1994026724A3 (en) * | 1993-05-18 | 1995-01-19 | Buckman Labor Inc | Preparation of n-cyanodithioimino-carbonates and 3-mercapto-5-amino-1h-1,2,4-triazole |
| RU2747082C2 (en) * | 2016-02-24 | 2021-04-26 | Доринг Интернэшнл Гмбх | Method of production of anti-viral drug |
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