Acetonitrile → 3-methyl-4-(methoxyacetamido)phenyl N-methylcarbamate

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Reaction Steps

3-methyl-4-aminophenyl N-methylcarbamate (3.6g. 0.02 mole) was dissolved in 35 ml. of benzene and 25 ml. of acetonitrile along with triethylamine (2.23g., 0.022 mole). To this stirred solution was added dropwise a solution of methoxyacetyl chloride in benzene. An exotherm to 45° C. was noted as solids began to form. Further heating at reflux for one hour yielded 2.4g. of Et3N.HCl upon filtration. Solvent removal from the filtrate under reduced pressure gave a product which was recrystallized from ethanol-water. The tan solid (2.4g.) melted at 129.5°-132° C. and the infrared spectrum (KBr) displayed the characteristic double carbonyl (5.7 μ and 5.95 μ).

Provenance & Evidence