Dimethyl Sulfoxide → HCID 57592135, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of oxalyl chloride (5.29 g, 41.4 mmol) in anhydrous dichloromethane (30 mL) at −78° C. was added anhydrous DMSO (6.2 mL, 87.4 mmol) dropwise with stirring in such a rate that the temperature was kept at −50 to −60° C. The solution was stirred for 15 min, then 2-fluoroethanol (1.62 mL, 27.6 mmol) was added dropwise and it was stirred for 15 min, diluted with dichloromethane (100 mL), followed by addition of dry Et3N (13.5 mL). The reaction mixture was stirred for 15 min, then allowed to warm to 0° C. and stirred at 0° C. for 2 h. To the reaction mixture was added a solution of 4-nitro-butyramide (3.04 g, 23 mmol) in CH2Cl2/THF (50 mL, 1:1). The reaction mixture was stirred at 0° C. for 3 h and then stirred at room temperature overnight. The mixture was concentrated to approximate 20 mL and poured into water (180 mL). It was extracted with ethyl acetate (12×40 mL), and the combined organic layers were dried and evaporated and the residue was purified by silica gel (CH2Cl2/EtOAc) to give 1.84 g (41%) of the titled product as a colorless viscous oil. 1H NMR (acetone-d6): 6.88 (bs, NH, 1H), 6.31 (bs, NH, 1H), 5.20-4.20 (m, 5H), 2.40-2.15 (m, 4H).

Provenance & Evidence