Tetrahedron letters

A simple and efficient biphasic method for the preparation of 4-nitrophenyl N-methyl-and N-alkylcarbamates

MA Peterson, H Shi, P Ke

Index: Peterson, Matt A.; Shi, Houguang; Ke, Pucheng Tetrahedron Letters, 2006 , vol. 47, # 20 p. 3405 - 3407

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Citation Number: 8

Abstract

Treatment of 4-nitrophenyl chloroformate with alkylammonium hydrochloride salts and solid anhydrous Na2CO3 in either CH2Cl2 or CH3CN gave 4-nitrophenyl N-methylcarbamate and other N-alkylcarbamate analogues in excellent yields. Of particular interest is the observation that 4-nitrophenyl N-methylcarbamate, a safer alternative to the highly toxic methyl isocyanate, is obtained in quantitative yield (⩾ 95% pure as determined by 1H ...