Dioctadecylamine → 3-(Dioctadecylcarbamoyl)benzene-1-sulfonyl chloride

Participants

Reaction Steps

To a stirred solution of 3-chlorosulfonylbenzoyl chloride (25.0 g, 1.1406 mol) in 250 ml of THF at 0° C. was added in one portion a cold suspension of dioctadecylamine (59.3 g, 0.1137 mol) and N,N-diisopropylethylamine (13.5 g, 0.1406 mol) in 500 ml of THF. The addition was exothermic to ≃10° C. The reaction was stirred without cooling overnight. The white insolubles were filtered and the filtrate poured into dilute hydrochloric acid. The aqueous mixture was extracted with ethyl acetate and the organic layer washed with water, dried over anhydrous magnesium sulfate and concentrated to dryness under aspirator pressure at 35° C. The resulting 68 g (90 percent) of yellow oil slowly crystallized. NMR was consistent for the product.

Provenance & Evidence