Methyl triflate → 3-(Imidazole-1-sulfonyl)-1-methyl-3H-imidazol-1-ium triflate

HRID 1969511Notes

Reaction equation

[S:1]([N:9]1[CH:13]=[CH:12][N:11]=[CH:10]1)([N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1)(=[O:3])=[O:2].[F:14][C:15]([F:22])([F:21])[S:16]([O:19]C)(=[O:18])=[O:17]>C(Cl)Cl>[F:14][C:15]([F:22])([F:21])[S:16]([O-:19])(=[O:18])=[O:17].[N:4]1([S:1]([N:9]2[CH:13]=[CH:12][N+:11]([CH3:15])=[CH:10]2)(=[O:2])=[O:3])[CH:8]=[CH:7][N:6]=[CH:5]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1,1′-sulfonyldiimidazole (3.50 g, 17.7 mmol) in DCM (75 mL) at about 0° C. was added methyl trifluoromethanesulfonate (1.94 mL, 17.7 mmol). The reaction mixture was stirred at about 0° C. for about 1 h, then warmed to ambient temperature and stirred for about 5 h. The solid was collected by vacuum filtration and washed with DCM (10 mL) to give 1-(1H-imidazol-1-ylsulfonyl)-3-methyl-1H-imidazol-3-ium trifluoromethanesulfonate (6.35 g, 98%) as a white solid: LC/MS (Table 1, Method a) Rt=0.082 min; MS m/z 213 (M+H)+.

Workup

temperaturewarmed to ambient temperature
stirringstirred for about 5 h
filtrationThe solid was collected by vacuum filtration
washwashed with DCM (10 mL)

Sources & evidence

ORD record: ord-e0677b92aa2e4c968b55397773d64953
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426411B2

Reaction notes

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