Water → 4-(Benzyloxy)-N,N,2-trimethyl-1-tosyl-1H-benzo[d]imidazole-6-carboxamide

HRID 2239291Notes

Reaction equation

HRID 2239291 reaction equation
[CH3:1][N:2]([CH3:23])[C:3]([C:5]1[CH:6]=[C:7]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:8]2[N:12]=[C:11]([CH3:13])[NH:10][C:9]=2[CH:14]=1)=[O:4].[H-].[Na+].[CH3:26][C:27]1[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1.O>CN(C)C=O>[CH3:23][N:2]([CH3:1])[C:3]([C:5]1[CH:6]=[C:7]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:8]2[N:12]=[C:11]([CH3:13])[N:10]([S:33]([C:30]3[CH:31]=[CH:32][C:27]([CH3:26])=[CH:28][CH:29]=3)(=[O:35])=[O:34])[C:9]=2[CH:14]=1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 68574634N,N,2-Trimethyl-4-[(phenylmethyl)oxy]-1H-benzimidazole-6-carboxamide

Product 1

HCID 672201744-(Benzyloxy)-N,N,2-trimethyl-1-tosyl-1H-benzo[d]imidazole-6-carboxamideYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of N,N,2-trimethyl-4-[(phenylmethyl)oxy]-1H-benzimidazole-6-carboxamide (928 mg, 3.0 mmol, STEP 5) in N,N-dimethylformamide (20 mL) was added sodium hydride (60% in mineral oil, 180 mg, 4.50 mmol) at 0° C. After stirring at room temperature for 30 minutes, the reaction mixture was cooled to 0° C. To the mixture was added 4-methylbenzenesulfonyl chloride (572 mg, 3.00 mmol) at 0° C., and the reaction mixture was stirred at room temperature for 2 hours. The mixture was poured into water, and the aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with water, dried over magnesium sulfate and concentrated in vacuum. The residue was purified by column chromatography on silica gel (gradient elution from dichloromethane only to ethyl acetate only) to afford the title compound as a white solid (1.00 g, 72%).

Workup

  1. temperaturethe reaction mixture was cooled to 0° C
  2. stirringthe reaction mixture was stirred at room temperature for 2 hours
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuum
  7. customThe residue was purified by column chromatography on silica gel (
  8. washgradient elution from dichloromethane only to ethyl acetate only)

Sources & evidence

ORD record
ord-62c4e3b3863c4cf2aba83b2ed36b0ade
Source dataset
uspto-grants-2010_05
Patent number
US07723321B2

Reaction notes

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