Dimethylformamide → (R)-1-(2-methyl-2-oxiranylmethyl)-4-nitro-2-(4-nitrophenylthio)imidazole

HRID 2221412Notes

Reaction equation

HRID 2221412 reaction equation
[N+:1]([C:4]1[N:5]=[C:6]([S:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)[NH:7][CH:8]=1)([O-:3])=[O:2].[CH3:19]N(C)C=O.C(=O)([O-])[O-].[K+].[K+].[F-].[Cs+].[C:32]([O:35][CH2:36][CH3:37])(=O)C>O>[CH3:19][C@@:36]1([CH2:37][N:7]2[CH:8]=[C:4]([N+:1]([O-:3])=[O:2])[N:5]=[C:6]2[S:9][C:10]2[CH:11]=[CH:12][C:13]([N+:16]([O-:18])=[O:17])=[CH:14][CH:15]=2)[CH2:32][O:35]1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 25953Cesium fluorideHCID 178526717HCID 178526717, compound

Product 1

HCID 86604370(R)-1-(2-methyl-2-oxiranylmethyl)-4-nitro-2-(4-nitrophenylthio)imidazoleYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Nitro-2-(4-nitrophenylthio)imidazole (500 mg) and N,N-dimethylformamide (1.6 ml) suspension of 2-methyl-2-oxiranylmethyl (S)-4-nitrobenzenesulfonate (513 mg), potassium carbonate (337 mg) and cesium fluoride (57 mg) were stirred at a room temperature for 1.5 days. Water and ethyl acetate were added to the reaction mixture and the organic layer was taken by separation. The ethyl acetate layer was washed with water and an aqueous solution being saturated with sodium chloride, then dried over anhydrous sodium sulfate. The residue obtained by removal of the solvent by distillation was purified by use of a basic silica gel column chromatography (eluent: n-hexane/ethyl acetate=13/7 to 11/9), there was obtained (R)-1-(2-methyl-2-oxiranylmethyl)-4-nitro-2-(4-nitrophenylthio)imidazole (456 mg, yield: 74%) as pale yellow powder product.

Workup

  1. customthe organic layer was taken by separation
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe residue obtained by removal of the solvent by distillation
  5. customwas purified by use of a basic silica gel column chromatography (eluent: n-hexane/ethyl acetate=13/7 to 11/9)

Sources & evidence

ORD record
ord-272e5dbf38604d95af362fe14af1371e
Source dataset
uspto-grants-2008_05
Patent number
US07368579B2

Reaction notes

Loading…