Dimethylformamide → 4-[(4-chlorophenyl)amino]-1-(4-methoxybenzyl)-3-methyl-1,3-dihydro-2H-benzimidazol-2-one

HRID 2235553Notes

Reaction equation

HRID 2235553 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:14]3[N:15]([CH3:19])[C:16](=[O:18])[NH:17][C:13]=3[CH:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[CH3:20][O:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Cl)=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]2[C:14]3[N:15]([CH3:19])[C:16](=[O:18])[N:17]([CH2:26][C:25]4[CH:28]=[CH:29][C:22]([O:21][CH3:20])=[CH:23][CH:24]=4)[C:13]=3[CH:12]=[CH:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 685813597-[(4-Chlorophenyl)amino]-1-methyl-1,3-dihydro-2H-benzimidazol-2-one

Product 1

HCID 685810534-[(4-chlorophenyl)amino]-1-(4-methoxybenzyl)-3-methyl-1,3-dihydro-2H-benzimidazol-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 7-[(4-chlorophenyl)amino]-1-methyl-1,3-dihydro-2H-benzimidazol-2-one (0.27 g, 1.0 mmol), 4-methoxybenzyl chloride (0.17 ml, 1.20 mmol), potassium carbonate (0.21 g, 1.50 mmol) and N,N-dimethylformamide (1 ml) was stirred at 70° C. for 100 min. The mixture was diluted with water (20 ml) and extracted with ethyl acetate (30 ml). The extract was washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was flash chromatographed eluting with a 15% ethyl acetate/hexanes to give 0.39 g (quant.) of the title compound as a powder.

Workup

  1. extractionextracted with ethyl acetate (30 ml)
  2. washThe extract was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customchromatographed
  6. washeluting with a 15% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-cce94f1420434a5ea14c95a341793c42
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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