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

HRID 1092891Notes

Reaction equation

HRID 1092891 reaction equation
[N+:1]([C:4]1[N:5]=[C:6]([S:9]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[NH:7][CH:8]=1)([O-:3])=[O:2].[CH3:21]N(C)C=O.C(=O)([O-])[O-].[K+].[K+].[F-].[Cs+].[C:34]([O:37][CH2:38][CH3:39])(=O)C>O>[CH3:21][C@@:38]1([CH2:39][N:7]2[CH:8]=[C:4]([N+:1]([O-:3])=[O:2])[N:5]=[C:6]2[S:9]([C:12]2[CH:13]=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][CH:17]=2)(=[O:11])=[O:10])[CH2:34][O:37]1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 25953Cesium fluorideHCID 178526725HCID 178526725, compound

Product 1

HCID 86604376(R)-1-(2-methyl-2-oxiranylmethyl)-4-nitro-2-(4-nitrobenzenesulfonyl)imidazoleYield 31%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Nitro-2-(4-nitrobenzenesulfonyl)imidazole (200 mg) and N,N-dimethylformamide (0.57 ml) suspension of 2-methyl-2-oxiranylmethyl(S)-4-nitrobenzenesulfonate (183 mg), potassium carbonate (120 mg) and cesium fluoride (20 mg) were stirred at a room temperature for 1.5 days. Water and ethyl acetate were added to the reaction mixture, and 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 silica gel column chromatography (eluent: n-hexane/ethyl acetate=11/9 to 1/1), there was obtained (R)-1-(2-methyl-2-oxiranylmethyl)-4-nitro-2-(4-nitrobenzenesulfonyl)imidazole (76 mg, yield: 31%) as white powdery product.

Workup

  1. customwas 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 silica gel column chromatography (eluent: n-hexane/ethyl acetate=11/9 to 1/1)

Sources & evidence

ORD record
ord-e657a733acc447ef8d5ef8f7997712f5
Source dataset
uspto-grants-2012_03
Patent number
US08129544B2

Reaction notes

Loading…