http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-769481-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_d037bc74e34c7d73dd883f208aef0518 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D277-32 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D277-32 |
| filingDate | 1953-05-08-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1957-03-06-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-769481-A |
| titleOfInvention | Thiazole carboxylic acid derivatives |
| abstract | The invention comprises a substituted thiazolecarboxylic acid hydrazide of the general formula: <FORM:0769481/IV(b)/1> wherein one of the symbols R, R1 or R2 denotes a mono- or dialkylcarbohydrazino or a nitrophenylcarbohydrazino, or an alkylidene- or carboxyalkylidenecarbohydrazino radical and the other two denote hydrogen, an alkyl radical of 1 to 6 carbon atoms or a phenyl radical. Such compounds are obtained by reacting a haloketone or haloaldehyde of the formula <FORM:0769481/IV(b)/2> in warm anhydrous conditions with or without a solvent, with a thioamide of the formula: <FORM:0769481/IV(b)/3> or by reacting a thiazole-2-carboxylic acid, acid halide or amide with a substituted hydrazine of the formula H2NNR3R4 wherein R3 and R4 represent hydrogen, an alkyl radical of 1 to 6 carbon atoms, a phenyl or nitrophenyl radical or R3 and R4 denote an alkylidene or carboxyalkylidene radical provided that R3 and R4 do not both represent hydrogen. Compounds of the first formula above where one of the symbols R, R1 and R2 represents an alkylidene- or carboxyalkylidene-hydrazino radical and the other two are as previously defined can be prepared by reacting a thiazolecarbohydrazide with a carbonyl compound of the formula R5COR6 wherein R5 and R6 may be alike or different and denote hydrogen, an alkyl radical of 1 to 6 carbon atoms, carboxy, or a carboxy alkyl radical. In examples: (1) thiazole-2-carboxylic acid hydrazide (prepared as described in Specification 769,482 is reacted with pyruvic acid to give pyruvic acid thiazole-2-carboxylhydrazone; (2 (a)) thiazole-2-carboxylic acid and 2 : 4-dinitrophenylhydrine are reacted to give 2-thiazolecarboxylic acid 2,4-dinitrophenylhydrazide; (2 (b)) thiazole-2-carboxamide and 1,1-diethylhydrazine are reacted to give a -thiazolecarboxylic acid 1,1-diethylhydrazide; (2 (c)) ethyl hydrazine and thiazole-2-carboxylic acid chloride are reacted to give thiazole-2-carboxylic acid ethylhydrazide; (3) a -keto-b -chlorobutyric acid and sodium bisulphite are reacted to give the addition compound, which with hydrazine gives a -keto-b -chlorobutyric acid hydrazide. This is reacted with thioformamide, and treatment of the 5-methyl-4-thiazolecarboxylic acid hydrazide obtained with acetone gives acetone 5 - methyl - 4 - thiazolecarbonylhydrazone; (4) 1-bromo-1-phenylacetone and acetone mono-thioamide oxalylhydrazone (from the reaction of mono-thio-oxamide and acetone hydrazone) are reacted to give 4-methyl-5-phenyl - thiazole - 2 - carbonylhydrazone; (5) ethyl mono - thio - oxamidate and phenylhydrazine are reacted and the product is reacted with chloracetaldehyde to give 2-thiazolecarboxylic acid phenylhydrazide. The haloaldehydes, haloketones and thioamides can be prepared by reaction of the appropriately substituted acid, anhydride, amide, ester or acid halide with a hydrazine of the formula H2NNR3R4 or with a hydrazone of the formula <FORM:0769481/IV(b)/4> where R5 and R6 are hydrogen or alkyl, carboxy or carbalkoxy radicals. |
| isCitedBy | http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-3234218-A http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-2951846-A |
| priorityDate | 1953-05-08-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
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