Oxalyl chloride → 4-(N,N-diethylaminomethyl)benzoyl chloride hydrochloride

Participants

Reaction Steps

To a well-stirred suspension consisting of 1.34 g. (5.0 mmole) of 4-(N,N-diethylaminomethyl)benzoic acid hydrochloride (the product of Preparation G) in 25 ml. of methylene chloride under a nitrogen atmosphere, there was added over a five-minute period a solution consisting of 1.5 g. (0.0118 mole) of oxalyl chloride dissolved in 5 ml. of methylene chloride. The resulting reaction mixture was refluxed for a period of 17 hours and then cooled to room temperature (~20° C.). The colorless solution so obtained was evaporated under reduced pressure, and the resulting residue was washed twice with methylene chloride and then stripped free of solvent to give a white solid product. In this way, there was readily obtained substantially pure 4-(N,N-diethylaminomethyl)benzoyl chloride hydrochloride, which was used in the next reaction step without any further purification being necessary. The yield of product was assumed to be quantitative.

Provenance & Evidence