1,2-Dimethoxyethane → 2,5-Pyrrolidinedione, 1-[[(trifluoromethyl)sulfonyl]oxy]-

Participants

Reaction Steps

N-Trifluoromethanesulfonyloxysuccinimide was prepared by the following procedure. To a dried flask equipped with a stirrer, under nitrogen, were added N-hydroxysuccinimide (2.10 g, 18.2 mmol), 60 mL of dried DME, and trifluoromethanesulfonyl chloride (2.00 mL, 18.7 mmol). The mixture was cooled in ice, and triethylamine (3 mL, 22 mmol) was added dropwise by syringe. After warming the reaction mixture to room temperature, 150 mL of methylene chloride was added and the organic layer was washed with water (3×100 mL) and dried. Evaporation of the solvent left 3.80 g of a white solid. Recrystallization from methylene chloride-hexane gave 3.22 g (71.6%) of N-trifluoromethanesulfonyloxysuccinimide: mp 122°-123°. A doubly recrystallized sample was prepared: mp 126°-127°; ir (KBr) 1695 (s), 1440 (s), 1230 (m), 1210 (m), 1140 (m), 1120 (m), 1030 (m), 790 (s), 590 (s); uv (CH3CN) 234 nm (shoulder) (ε=130); nmr (CDCl3) 2.85 (s); 19F nmr -71.54 ppm (s); mass spectrum 246.9781 (calcd for C5H4NO5F3S: 246.9762). Anal. Calcd for C5H4NO5F3S: C, 24.30; H, 1.63; N, 5.67; O, 32.37; F, 23.06; S, 12.97. Found: C, 24.16; H, 1.57; N, 5.95.

Provenance & Evidence