2-(Methylamino)ethanol → N-(2-Hydroxyethyl)-4-methoxy-N,2,6-trimethylbenzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

Triethylamine (213 ml, 1,512.5 mmol) was added to a solution of 2-(methylamino)ethanol (53.5 ml, 665.5 mmol) in MC (1,250 ml) and the mixture was cooled to 0° C. A solution of 4-methoxy-2,6-dimethylbenzene-1-sulfonyl chloride (142 g, 605 mmol) [see AC5, Stage 1] in MC (750 ml) was then slowly added dropwise. The reaction mixture was stirred at room temperature for 2 hours. The organic phase was then washed with aqueous 0.5 M HCl (800 ml) and water (2×1,000 ml). The combined organic phases were dried with Na2SO4, filtered and concentrated in vacuo. Purification was carried out by chromatography on silica gel (heptane/ethyl acetate 1:1). The yield was 116.3 g (70%).

Provenance & Evidence