Methylamine → 4-fluoro-N-methylbenzene-1-sulfonamide

Participants

Reaction Steps

A mixture of 125 ml of methylamine (0.25 molar) in tetrahydrofuran and 13.9 ml (0.10 mol) of triethylamine was chilled in an ice bath. To this chilled solution was added dropwise 19.4 g (0.10 mol) of 4-fluorobenzenesulfonyl chloride in 150 ml of CH2Cl2 was added and the mixture refluxed for 2 hours and then stirred overnight at room temperature. The mixture was with CH2Cl2, washed with H2O, 2N citric acid, brine and dried (Na2SO4). The solution was filtered through a pad of hydrous magnesium silicate and the filtrate concentrated to dryness under vacuum to give 18.0 g of white solid, mp 67-70° C.

Provenance & Evidence