Dimethylformamide → (R)-2-(2-chloro-6-nitrophenylthio)-1-(2-methyl-2-oxiranylmethyl)-4-nitroimidazole

HRID 2221414Notes

Reaction equation

HRID 2221414 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[S:11][C:12]1[NH:13][CH:14]=[C:15]([N+:17]([O-:19])=[O:18])[N:16]=1.[CH3:20]N(C)C=O.C(=O)([O-])[O-].[K+].[K+].[F-].[Cs+].[C:33]([O:36][CH2:37][CH3:38])(=O)C>O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[S:11][C:12]1[N:13]([CH2:20][C@:37]2([CH3:38])[CH2:33][O:36]2)[CH:14]=[C:15]([N+:17]([O-:19])=[O:18])[N:16]=1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 25953Cesium fluorideHCID 178526859HCID 178526859, compound

Product 1

HCID 86604374(R)-2-(2-chloro-6-nitrophenylthio)-1-(2-methyl-2-oxiranylmethyl)-4-nitroimidazoleYield 61%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(2-Chloro-6-nitrophenylthio)-4-nitroimidazole (113 mg) and N,N-dimethylformamide (0.5 ml) suspension of 2-methyl-2-oxiranylmethyl (S)-4-nitrobenzenesulfonate (119 mg), potassium carbonate (71 mg) and cesium fluoride (11 mg) were stirred at a room temperature for 3.5 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=11/9 to 1/1), then there was obtained (R)-2-(2-chloro-6-nitrophenylthio)-1-(2-methyl-2-oxiranylmethyl)-4-nitroimidazole (85 mg, yield: 61%) as yellow powdery 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=11/9 to 1/1)

Sources & evidence

ORD record
ord-e6cd37f2a24a4c41936f42dc678bc5f7
Source dataset
uspto-grants-2008_05
Patent number
US07368579B2

Reaction notes

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