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

Treatment of 4-nitrophenyl chloroformate with alkylammonium hydrochloride salts and solid anhydrous Na 2CO 3 in either CH 2Cl 2 or CH 3CN gave 4-nitrophenyl N-methylcarbamate and other N-alkylcarbamate analogues in excellent yields. Of particular interest is the observation that 4-nitrophenyl N-meth...

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Bibliographic Details
Published inTetrahedron letters Vol. 47; no. 20; pp. 3405 - 3407
Main Authors Peterson, Matt A., Shi, Houguang, Ke, Pucheng
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 15.05.2006
Elsevier
Subjects
4-Nitrophenyl N-methylcarbamate
Chemistry
Chemistry, Organic
Methyl isocyanate
N-Methylcarbamates
N-Methylureas
Physical Sciences
Science & Technology
N-Methylcarbamates
N-Methylureas
Methyl isocyanate
4-Nitrophenyl N-methylcarbamate
N-methylcarbamates
ROTATION
methyl isocyanate
N-methylureas
ANALOGS
CONVENIENT METHOD
BARRIERS
4-nitrophenyl
TRANSESTERIFICATION
CARBAMATE
ISOCYANATE TOXICITY
ANTAGONISTS
DERIVATIVES
N-methylcarbamate
UREA
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Summary:Treatment of 4-nitrophenyl chloroformate with alkylammonium hydrochloride salts and solid anhydrous Na 2CO 3 in either CH 2Cl 2 or CH 3CN 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 NMR) after simple filtration and solvent evaporation.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2006.03.075