Methyl iodide → Methyl 4-[14-(trimethylsilyl)tetradecylamino]benzoate

Participants

Reaction Steps

A solution of 7.0 g. of 4-[14-(trimethylsilyl)tetradecylamino)benzoic acid in 25 ml. of hexamethylphosphoramide is added to a stirred mixture of 0.800 g. of sodium hydride (57% in mineral oil) and 25 ml. of hexamethylphosphoramide. The solution which forms after one hour is treated with 11.0 g. of methyl iodide and is then stirred at 25° C. for 18 hours. Dilution with water followed by filtration affords a white solid which is crystallized from ethanol to yield the product as a white solid.

Provenance & Evidence