US EPA

3746906 

Journal Article 

Synthesis of 2-substituted-3-oxo.3-[(aryloxycarbonyl)amino]propanoic acids, ethyl 3-([(1E)-ethoxy(aryloxy)methylene]aminol-2-substituted-3-oxopropanoate, (1Z, 2Z) [chloro(aryloxy)methylenelhydrazine and structurally related compounds from the reactions of alkyl or aryl malonyl chloride with aryl cyanates 

Sheat, MA; Al-Rawi, JMA 

2005 

Yes 

Asian Journal of Chemistry
ISSN: 0970-7077
EISSN: 0975-427X 

17 

2 

798-810 

English 

WOS:000229096600024 

Treatment of the reaction mixture of alkyl or arylmalonyl chlorides and aryl cyanates with water give 2-substituted-3-oxo-3-[(phenoxycarbonyl)amino] propanoic acid (1); while with absolute ethanol ethyl 3-{[(1E)-ethoxy (aryloxy)methylene]amino}-2-substituted-3-oxopropanoate (3) is produced. Aryl 3-chloro-2-substituted-3-oxoprop-anoylcarbamate (2) was obtained from the reaction of alkyl or aryl malonyl chlorides with aryl carbamate. Compound 1 was also obtained from the reaction of compound 2 with water. A mechanism is suggested for the formation of compounds 1 and 3. The (1Z, 2Z) [chloro(aryloxy)methylene]hydrazine (5) is isolated from the reaction of alkyl or aryl malonyl chloride (1 mol) with aryl cyanate (2 mol). Product 5 is also prepared from an equimolar reaction of acetyl or benzoyl chloride with aryl cyanates. 

synthesis; malonyl chloride; aryl cyanate