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

HRID 551018Notes

Reaction equation

HRID 551018 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 1420, 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 1420
  4. customdried in vacuo

Sources & evidence

ORD record
ord-fdd99f51e9b74ae89ee48977b128c796
Source dataset
uspto-grants-2011_05
Patent number
US07947677B2

Reaction notes

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