Dichloromethane → HCID 178484053, compound

Participants

Reaction Steps

A heterogenous mixture of 1.59 g (4.35 mmol) of trans-N-(4-hydroxymethyl-cyclohexylmethyl)-N-methyl-4-trifluoromethyl-benzenesulfonamide (example 5.1), 5.0 ml of dichloromethane , 37.2 g (174 mmol) of (E)-1,4-dibromo-2-butene, 15.0 ml of 50% w/w sodium hydroxide solution and 0.44 g (1.3 mmol) of tetrabutylammonium hydrogensulfate was stirred vigorously at room temperature for 3 days. Afterwards, 30 ml of deionized water were added and the reaction mixture was extracted with 3 portions of n-hexane. The combined organic phases were then washed with water (3 times), 1 N aqueous hydrochloric acid solution, saturated aqueous sodium bicarbonate solution, brine and were finally dried over magnesium sulfate and evaporated under reduced pressure. The excess of the (E)-1,4-dibromo-2-butene was distilled off under reduced pressure (0.5 torr) at 100° C. The residue thus obtained was chromatographed on silicagel with a 3:1 v/v mixture of dichloromethane and hexane as the eluent giving 1.51 g (69.6%) of trans-N-[4-(4-bromo-(E)-but-2-enyloxymethyl)-cyclohexylmethyl]-N-methyl-4-trifluoromethyl-benzenesulfonamide as pale yellow solid, MS: 515 (MNH4+, 1Br).

Provenance & Evidence