GB567353A - Improvements in the manufacture of tetrazole compounds - Google Patents
Improvements in the manufacture of tetrazole compoundsInfo
- Publication number
- GB567353A GB567353A GB1400443A GB1400443A GB567353A GB 567353 A GB567353 A GB 567353A GB 1400443 A GB1400443 A GB 1400443A GB 1400443 A GB1400443 A GB 1400443A GB 567353 A GB567353 A GB 567353A
- Authority
- GB
- United Kingdom
- Prior art keywords
- groups
- substituted
- group
- cssr1
- phenyl
- 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 tetrazole compounds Chemical class 0.000 title abstract 10
- 238000004519 manufacturing process Methods 0.000 title 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 6
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 abstract 4
- 229910052783 alkali metal Inorganic materials 0.000 abstract 3
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 2
- 230000020477 pH reduction Effects 0.000 abstract 2
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 abstract 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 125000006267 biphenyl group Chemical group 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 150000004985 diamines Chemical class 0.000 abstract 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract 1
- 235000019441 ethanol Nutrition 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- JQIDGEXIZBQJKS-UHFFFAOYSA-N methyl n-cyclohexylcarbamodithioate Chemical compound CSC(=S)NC1CCCCC1 JQIDGEXIZBQJKS-UHFFFAOYSA-N 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 235000010755 mineral Nutrition 0.000 abstract 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 abstract 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000011877 solvent mixture Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 150000003536 tetrazoles Chemical class 0.000 abstract 1
- 125000003396 thiol group Chemical group [H]S* 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1.2.3.4-Tetrazole compounds, containing a substituted or unsubstituted hydrocarbon group in the 1-position and a mercapto group in the 5-position and tautomers thereof, are made, in the form of their alkali metal salts, by reaction of a compound of the formula R.NH.CSSR1, where R and R1 represent substituted or unsubstituted hydrocarbon groups, with an alkali metal azide. The free tetrazoles are obtained by acidification of the alkali-metal salts in solution. The mercaptan R1SH, split off during the reaction, constitutes a valuable by-product. In examples: 1-methyl-, phenyl-, cyclohexanyl-, (21 - methoxy) - phenyl-, (41 - chloro) phenyl-, benzyl- and a - and b -naphthyl-5-mercapto-1.2.3.4-tetrazoles are made from the corresponding N-substituted dithiocarbamic acid methyl esters and sodium azide in an aqueous ethyl alcohol medium with subsequent acidification. Any other substantially inert solvent or solvent mixture may be used. Other specified groups, R, are ethyl or higher alkyl, naphthylmethyl, diphenyl and cyclopentanyl and other substituents which such groups may carry are halogen atoms, nitro, amino, substituted amino, hydroxy, alkoxy and hydroxyalkyl groups. Also the group R may carry a second -NH.CSSR1 group, whereupon bis-tetrazole compounds are formed. Thiocarbamic esters of the above general formula are prepared by reaction of an amine of the formula R.NH2 with carbon disulphide in the presence of a strong base, e.g. caustic soda, to give, e.g. a compound R.NH.CSSNa, and treating this with an ester, R1X, where X represents the residue of a strong acid, e.g. a mineral acid or p-toluene sulphonic acid. Where a diamine such as p-phenylene diamine or benzidine is used, the product contains two -NH.CSSR1 groups. Thus, N-cyclohexanyl dithiocarbamic acid methyl ester is prepared from cyclohexylamine, carbon disulphide, caustic soda and dimethyl sulphate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1400443A GB567353A (en) | 1943-08-27 | 1943-08-27 | Improvements in the manufacture of tetrazole compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1400443A GB567353A (en) | 1943-08-27 | 1943-08-27 | Improvements in the manufacture of tetrazole compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB567353A true GB567353A (en) | 1945-02-09 |
Family
ID=10033258
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1400443A Expired GB567353A (en) | 1943-08-27 | 1943-08-27 | Improvements in the manufacture of tetrazole compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB567353A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2370739A1 (en) * | 1976-09-02 | 1978-06-09 | Smithkline Corp | 1-CARBOXYMETHYLTHIOETHYL-TETRAZOLE-5-THIOL |
| EP0019308A1 (en) * | 1977-06-24 | 1980-11-26 | Smithkline Beckman Corporation | Tetrazole derivatives and a process for their preparation |
| FR2510999A1 (en) * | 1981-06-29 | 1983-02-11 | Sandoz Ag | NEW TETRAZOLIC DERIVATIVES |
-
1943
- 1943-08-27 GB GB1400443A patent/GB567353A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2370739A1 (en) * | 1976-09-02 | 1978-06-09 | Smithkline Corp | 1-CARBOXYMETHYLTHIOETHYL-TETRAZOLE-5-THIOL |
| EP0019308A1 (en) * | 1977-06-24 | 1980-11-26 | Smithkline Beckman Corporation | Tetrazole derivatives and a process for their preparation |
| FR2510999A1 (en) * | 1981-06-29 | 1983-02-11 | Sandoz Ag | NEW TETRAZOLIC DERIVATIVES |
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