Sodium hydride → HCID 57141444, compound

Participants

Reaction Steps

Sodium hydride (1.32 g., 80% w/w dispersion in mineral oil) was added in portions to a solution of di-(4-chlorophenyl)methyloxyacetic acid (6.2 g.) in dry dimethylformamide (30 ml.) cooled below 30°. The mixture was stirred for 15 minutes at ambient temperature after the addition was complete and N,N-dimethyl-2-chloroethylamine hydrochloride (2.88 g.) was then added. The mixture was heated at 100° for 16 hours, cooled and then poured into water (200 ml.). The aqueous mixture was extracted with ether. The extracts were washed with aqueous acetic acid (2×100 ml. of a 10% v/v solution). The acid washings were basified to pH 11-12 with aqueous sodium hydroxide solution and extracted with ether. The ether extracts were dried (MgSO4) and evaporated. The residual oil thus obtained was mixed with an excess of an ethereal solution of maleic acid. The solid thus formed was separated by filtration and crystallised from ethyl acetate to give 2-dimethylamino-ethyl di-(4-chlorophenyl)methyloxyacetate as the maleate salt, m.p. 103°-104°, having the composition C19H21O3NCl2.C4H4O4 by microanalysis, and in 43% yield.

Provenance & Evidence