Methyl iodide → benzyl N-(4-iodophenyl)-N-methylcarbamate

Participants

Reaction Steps

A stirred solution of N-benzyloxycarbonyl-4-iodoaniline (11.5 g, Reference Example 27) in dimethylformamide (70 ml) was treated portionwise with sodium hydride (⅙ g of a 60% dispersion in oil), under nitrogen and at room temperature. When effervescence had ceased methyl iodide (6.3 g) was added and the mixture was stirred at room temperature for 2 hours, after which it was partitioned between ethyl acetate and water. The organic phase was separated, then dried over magnesium sulphate and then evaporated to give the title compound (11.5 g) as a pink oil.

Provenance & Evidence