Water → Methyl {3-[(4-methylphenyl)sulfonyl]-7-nitro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl}acetate

HRID 2426178Notes

Reaction equation

HRID 2426178 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[C:19]([N+:20]([O-:22])=[O:21])[C:14]=3[NH:13][C:12]2=[O:23])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:31][C:32]([O:34][CH3:35])=[O:33].O>CN(C=O)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[C:19]([N+:20]([O-:22])=[O:21])[C:14]=3[N:13]([CH2:31][C:32]([O:34][CH3:35])=[O:33])[C:12]2=[O:23])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 576637451-[(4-Methylphenyl)sulfonyl]-4-nitro-1,3-dihydro-2H-benzimidazol-2-one

Product 1

HCID 57663776Methyl {3-[(4-methylphenyl)sulfonyl]-7-nitro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl}acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 1-[(4-methylphenyl)sulfonyl]-4-nitro-1,3-dihydro-2H-benzimidazol-2-one from Step B (500 mg, 1.50 mmol) in DMF (50 mL) was added potassium carbonate (207 mg, 1.50 mmol) and the resulting mixture was stirred at ambient temperature for 10 min. Methyl bromoacetate (252 mg, 1.65 mmol) was added dropwise and the reaction mixture was stirred for 1 h, then poured into H2O (50 mL). The resulting precipitate was isolated by filtration, washed with H2O, and dried in vacuo to give the title compound. MS: m/z=406 (M+1).

Workup

  1. stirringthe reaction mixture was stirred for 1 h
  2. customThe resulting precipitate was isolated by filtration
  3. washwashed with H2O
  4. customdried in vacuo

Sources & evidence

ORD record
ord-796de5bdb3324546abd9e9ca6382564d
Source dataset
uspto-grants-2011_06
Patent number
US07968540B2

Reaction notes

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