Sodium hydride → HCID 69740515, compound

HRID 1071454Notes

Reaction equation

HRID 1071454 reaction equation
[CH2:1]([N:5]([CH2:16][C:17]1[NH:21][C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[N:18]=1)[C:6](=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:8]=1[F:14])[CH2:2][CH2:3][CH3:4].[H-].[Na+].[Cl:28][CH2:29]/[CH:30]=[CH:31]\[CH2:32]Cl>CC(N(C)C)=O.C(OCC)(=O)C>[F:14][C:8]1[C:9]([F:13])=[CH:10][CH:11]=[CH:12][C:7]=1[C:6]([N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH:16]([CH2:32][CH:31]=[CH:30][CH2:29][Cl:28])[C:17]1[NH:18][C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=1)=[O:15]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 64321151,4-Dichloro-cis-2-buteneHCID 22394018N-butyl-N-(1H-benzoimidazol-2-ylmethyl)-2,3-difluorobenzamide

Product 1

HCID 69740515HCID 69740515, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

N-butyl-N-(1H-benzoimidazol-2-ylmethyl)-2,3-difluorobenzamide (226 mg, 0.66 mmol) was dissolved in 3 mL dimethylacetamide at room temperature. Sodium hydride (29 mg, 0.72 mmol, 60% oil dispersion) was added and the reaction mixture stirred 5 minutes. Cis-1,4-Dichloro-2-butene was added and the reaction mixture stirred 90 minutes. The reaction mixture was diluted with 10 mL ethyl acetate, placed in a separatory funnel and washed 1×10 mL H2O then 1×10 mL brine. The organic phase was dried over MgSO4, filtered, concentrated, then purified by flash chromatography eluting with 1/1 ethyl acetate/hexane to afford 206 mg 2,3-difluoro-N-butyl-N-[(4-chlorobut-2-enyl)-1H-benzoimidazol-2-ylmethyl]-benzamide.

Workup

  1. stirringthe reaction mixture stirred 90 minutes
  2. customplaced in a separatory funnel
  3. washwashed 1×10 mL H2O
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash chromatography
  8. washeluting with 1/1 ethyl acetate/hexane

Sources & evidence

ORD record
ord-dec45ae1438d4949a46841b7dc461363
Source dataset
uspto-grants-2005_06
Patent number
US06906075B2

Reaction notes

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