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

HRID 1403709Notes

Reaction equation

HRID 1403709 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>[O-:19][S:16]([C:15]([F:22])([F:21])[F:14])(=[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

4

Reactant 2

HCID 9526Methyl triflateHCID 816091,1'-sulphonylbis-1H-imidazole

Product 1

HCID 117281493-(Imidazole-1-sulfonyl)-1-methyl-3H-imidazol-1-ium triflateYield 196.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1,1′-sulfonyldiimidazole (1.50 g, 7.57 mmol) in DCM (25 mL) at 0° C. was treated dropwise with methyl trifluoromethane sulfonate (830 μL, 7.57 mmol) and stirred cold for 3 hours. The precipitate was collected by filtration washing with DCM and air-dried to give the title compound (2.70 g, 98%) as a white solid solid. LCMS (m/z, Method A) ES+ 213.0 [M+1]+.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashing with DCM
  3. customair-dried

Sources & evidence

ORD record
ord-56f8103aae594be182a4b3f2607a6571
Source dataset
uspto-grants-2014_12
Patent number
US08912219B2

Reaction notes

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