Sodium Bicarbonate → N-butyl-N-(1H-benzoimidazol-2-ylmethyl)-2,3-difluorobenzamide

HRID 1071453Notes

Reaction equation

HRID 1071453 reaction equation
[CH2:1]([NH:5][CH2:6][C:7]1[NH:8][C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[N:11]=1)[CH2:2][CH2:3][CH3:4].C([O-])(O)=O.[Na+].[F:21][C:22]1[C:30]([F:31])=[CH:29][CH:28]=[CH:27][C:23]=1[C:24](Cl)=[O:25]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([N:5]([CH2:6][C:7]1[NH:8][C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[N:11]=1)[C:24](=[O:25])[C:23]1[CH:27]=[CH:28][CH:29]=[C:30]([F:31])[C:22]=1[F:21])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 5195492,3-Difluorobenzoyl chlorideHCID 131694082-Butylaminomethylbenzimidazole

Product 1

HCID 22394018N-butyl-N-(1H-benzoimidazol-2-ylmethyl)-2,3-difluorobenzamideYield 58.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-butylaminomethylbenzimidazole (2.6 g, 13 mmol) was dissolved in 30 mL toluene. Saturated NaHCO3 solution (30 mL) was added followed by 2,3-difluorobenzoyl chloride (1.3 mL, 10 mmol). The reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was diluted with 100 mL ethyl acetate then washed 1×100 mL 1N NaOH followed by 1×100 mL H2O. The organic phase was dried over MgSO4, filtered, and then concentrated. The residue was purified by flash chromatography eluting with 1/1 ethyl acetate/hexane followed by ethyl acetate to afford 2.0 g N-butyl-N-(1H-benzoimidazol-2-ylmethyl)-2,3-difluorobenzamide.

Workup

  1. washthen washed 1×100 mL 1N NaOH
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography
  6. washeluting with 1/1 ethyl acetate/hexane

Sources & evidence

ORD record
ord-1c8f55698ef9426792c6276dac21d453
Source dataset
uspto-grants-2005_06
Patent number
US06906075B2

Reaction notes

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