Benzenesulfonyl chloride → HCID 70574288, compound

Participants

Reaction Steps

A mixture of 1-(3-aminopropyl)-3-(1-imidazolylmethyl)indole (1.27 g) and benzenesulphonyl chloride (0.88 g) in pyridine (15 ml) was heated on a steam bath for 2 hours and then evaporated to dryness. The residue was treated with an aqueous solution of sodium bicarbonate and the mixture was extracted with ethyl acetate (2×50 ml). The combined extracts were washed with water and dried (Na2SO4). The solvent was evaporated and the residue was chromatographed on silica gel. The column was first eluted with chloroform to remove a small amount of impurity and then the product was eluted with a mixture of chloroform and methanol (20:1). Evaporation of the product containing fractions gave an oil which crystallised on standing. The product was recrystallised from ethyl acetate containing a trace of methanol to give 1-(3-benzenesulphonylaminopropyl)-3-(1-imidazolylmethyl)indole (0.58 g), m.p. 130°-131° C. Found: C, 63.71; H, 5.58; N, 14.03. C21H22N4O2S requires: C, 63.93; H, 5.62; N, 14.20.

Provenance & Evidence