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

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.

1. customN-Trifluoromethanesulfonyloxysuccinimide was prepared by the following procedure
2. customTo a dried flask equipped with a stirrer, under nitrogen
3. temperatureThe mixture was cooled in ice
4. washthe organic layer was washed with water (3×100 mL)
5. customdried
6. customEvaporation of the solvent
7. waitleft 3.80 g of a white solid
8. customRecrystallization from methylene chloride-hexane

ORD record

ord-1e98f0293261439ea3fea7e6a8747817

Source dataset

uspto-grants-1983_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04371605