GB801394A - 1:3:4-thiadiazoles and their preparation - Google Patents
1:3:4-thiadiazoles and their preparationInfo
- Publication number
- GB801394A GB801394A GB2505755A GB2505755A GB801394A GB 801394 A GB801394 A GB 801394A GB 2505755 A GB2505755 A GB 2505755A GB 2505755 A GB2505755 A GB 2505755A GB 801394 A GB801394 A GB 801394A
- Authority
- GB
- United Kingdom
- Prior art keywords
- thiadiazole
- mercapto
- treated
- prepared
- chlorine gas
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 9
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 4
- -1 alkyl chloroformate Chemical compound 0.000 abstract 4
- GDGIVSREGUOIJZ-UHFFFAOYSA-N 5-amino-3h-1,3,4-thiadiazole-2-thione Chemical compound NC1=NN=C(S)S1 GDGIVSREGUOIJZ-UHFFFAOYSA-N 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- 239000007858 starting material Substances 0.000 abstract 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 abstract 2
- 230000001476 alcoholic effect Effects 0.000 abstract 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 2
- 239000007787 solid Substances 0.000 abstract 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000000908 ammonium hydroxide Substances 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- KIWBRXCOTCXSSZ-UHFFFAOYSA-N hexyl carbonochloridate Chemical class CCCCCCOC(Cl)=O KIWBRXCOTCXSSZ-UHFFFAOYSA-N 0.000 abstract 1
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 150000003456 sulfonamides Chemical class 0.000 abstract 1
- 239000000725 suspension Substances 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Abstract
The invention comprises 2-alkoxycarbamido-5 - sulphonamido - 1 : 3 : 4 - thiadiazoles of the general formula <FORM:0801394/IV (b)/1> where R is an alkyl (including cycloalkyl) or aralkyl group containing not more than 18 carbon atoms, and the manufacture thereof by treating 2-amino-5-mercapto-1 : 3 : 4-thiadiazole with one equivalent of an alkyl chloroformate in the presence of a hydrogen chloride abstractor, reacting the resulting 2-alkoxy carbamido-5-mercapto-1 : 3 : 4-thiadiazole in aqueous acetic acid solution with a slight excess of chlorine gas and the resulting sulphonchloride with liquid ammonia or concentrated ammonium hydroxide. By reacting the starting material with two equivalents of an alkyl chloroformate a diacyl-1 : 3 : 4-thiadiazole may be prepared which on reaction with chlorine gas yields the sulphonchloride above. In an example, sufficient pyridine is added to a suspension of 2-amino-5-mercapto-1 : 3 : 4-thiadiazole in dimethylaniline to dissolve the solid. The solution is ice-cooled and ethyl chloroformate added. The 2-ethoxycarbamido - 5 - mercapto - 1 : 3 : 4 - thiadiazole so prepared is suspended in 33 per cent aqueous acetic acid, cooled to 0 DEG C. and treated with chlorine gas. The resultant solid is then treated with liquid ammonia to yield 2-ethoxycarbamido-5-sulphonamido-1 : 3 : 4-thiadiazole. In a similar manner is prepared 2-methoxy-, 2-benzyloxy-, 2-n-propoxy-, 2-n-butoxy-, 2-n-amyloxy- and 2-n-hexyloxycarbamido-5-sulphonamido-1 : 3 : 4-thiadiazoles. Examples are also given of the reaction of the starting material with ethyl, benzyl, n-amyl, and n-hexylchloroformates in pyridine and at 0 DEG C. to form the corresponding diacyl compounds. These are suspended in 50 per cent aqueous acetic acid and treated with chlorine gas, the sulphonchlorides so formed being treated, as above, with liquid ammonia to yield the sulphonamides. Starting material. 2-Amino-5-mercapto-1 : 3 : 4-thiadiazole may be prepared by reacting thiosemicarbazide with carbon disulphide in aqueous alcoholic ethylene glycol solution in the presence of potassium hydroxide or in substantially anhydrous alcoholic media in the presence of an alkali. An example is given in the Provisional Specification.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2505755A GB801394A (en) | 1955-08-31 | 1955-08-31 | 1:3:4-thiadiazoles and their preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2505755A GB801394A (en) | 1955-08-31 | 1955-08-31 | 1:3:4-thiadiazoles and their preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB801394A true GB801394A (en) | 1958-09-10 |
Family
ID=10221516
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2505755A Expired GB801394A (en) | 1955-08-31 | 1955-08-31 | 1:3:4-thiadiazoles and their preparation |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB801394A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993005029A1 (en) * | 1991-08-28 | 1993-03-18 | University Of Iowa Research Foundation | Topical ophthalmic imino substituted 2-imino-3-methyl-δ4-1,3,4-thiadiazoline-5-sulfonamides carbonic anhydrase inhibitors |
-
1955
- 1955-08-31 GB GB2505755A patent/GB801394A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993005029A1 (en) * | 1991-08-28 | 1993-03-18 | University Of Iowa Research Foundation | Topical ophthalmic imino substituted 2-imino-3-methyl-δ4-1,3,4-thiadiazoline-5-sulfonamides carbonic anhydrase inhibitors |
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