85210-15-7

Upstream product

• 102-09-0 bis(phenyl) carbonate 
• 4114-31-2 ethylhydrazine carboxylate 
• 1885-14-9 phenyl chloroformate 

Downstream Products

• 13482-66-1 ethyl 2-(methylcarbamoyl)hydrazine-1-carboxylate 
• 25544-79-0 ethyl 2-(butylcarbamoyl)hydrazine-1-carboxylate 
• 57965-06-7 ethyl 2-(benzylcarbamoyl)hydrazine-1-carboxylate 
• 17696-94-5 ethyl 2-(tert-butylcarbamoyl)hydrazine-1-carboxylate 

Relevant academic research and scientific papers

Alternative synthetic routes to N-methyl-1,2,4-triazoline-3,5-dione (MeTAD) and other triazolinedione derivatives

N-Methyl-1,2,4-triazoline-3,5-dione (MeTAD) is a powerful electrophile and a versatile synthetic reagent. In this Letter we describe two methods for the synthesis of N-methylurazole, the direct precursor to MeTAD, on gram scales and in good yields. Both methods provide pure urazole while avoiding the necessity of large scale purification via column chromatography or recrystallization. One of the methods proved to be amenable for the synthesis of derivatives other than N-methyl.

Preparation of 2-(alkylcarbamoyl)hydrazine-1-carboxylic acid alkyl ester or its corresponding urazole salt

The present invention relates to the preparation of 2-(alkylcarbamoyl)hydrazine-1-carboxylic acid alkyl ester or its corresponding urazole salt. The present invention relates to 2-(alkylcarbamoyl)hydrazine-1-alkyl carboxylate or its corresponding derivative alkyl-4H-1,2,4-triazole-3,5-diol salt (urine Azole salt) preparation. This is particularly advantageous because it uses a one-pot reaction and uses alkyl acetate as the solvent in steps a) and b) of its synthesis.

Sustainable synthesis routes towards urazole compounds

Sustainable synthesis routes towards urazoles, the precursor molecules for triazolinediones, are reported. Not only is the use of isocyanates avoided, but the applied synthetic procedures are also mostly solvent-free, high yielding and performed in an equimolar manner. Two complementary synthesis routes have been developed starting from a wide range of amines, both based on the use of diphenyl carbonate. The first method, which is particularly suitable for the synthesis of bulk urazoles, such as butyl, cyclohexyl or benzyl urazole, is performed in bulk in a one-pot fashion and generally results in yields between 87% and 96%. The second synthesis route, with yields up to 95%, focusses on the implementation of functionalities in the urazole structure and offers the possibility to generate bifunctional urazole compounds.