Methyl triflate → 1-(3,3-difluoroazetidin-1-ylsulfonyl)-3-methyl-1H-imidazol-3-ium trifluoromethanesulfonate

HRID 1969513Notes

Reaction equation

[F:1][C:2]1([F:14])[CH2:5][N:4]([S:6]([N:9]2[CH:13]=[CH:12][N:11]=[CH:10]2)(=[O:8])=[O:7])[CH2:3]1.[F:15][C:16]([F:23])([F:22])[S:17]([O:20]C)(=[O:19])=[O:18]>C(Cl)Cl>[F:15][C:16]([F:23])([F:22])[S:17]([O-:20])(=[O:19])=[O:18].[F:14][C:2]1([F:1])[CH2:5][N:4]([S:6]([N:9]2[CH:13]=[CH:12][N+:11]([CH3:16])=[CH:10]2)(=[O:8])=[O:7])[CH2:3]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1-(3,3-difluoroazetidin-1-ylsulfonyl)-1H-imidazole (0.500 g, 2.24 mmol) in DCM (5 mL) at about 0° C. was added methyl trifluoromethanesulfonate (0.27 mL, 2.46 mmol) dropwise over about 3 min. The reaction mixture was stirred at about 0° C. for about 2 h. The solid was collected by vacuum filtration, washed with DCM (10 mL), and dried under vacuum to give 1-(3,3-difluoroazetidin-1-ylsulfonyl)-3-methyl-1H-imidazol-3-ium trifluoromethanesulfonate (0.79 g, 90%) as a white solid: LC/MS (Table 1, Method c) Rt=1.12 min; MS m/z 238 (M+H)+.

Workup

filtrationThe solid was collected by vacuum filtration
washwashed with DCM (10 mL)
customdried under vacuum

Sources & evidence

ORD record: ord-8d63c9db65304189b03d9a81bbb2a3af
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426411B2

Reaction notes

Loading…