Sodium hydride → HCID 44430229, compound

HRID 2043252Notes

Reaction equation

HRID 2043252 reaction equation
[Cl:1][C:2]1[C:15]([Cl:16])=[CH:14][C:5]2[NH:6][C:7]([CH2:9][C:10]([F:13])([F:12])[F:11])=[N:8][C:4]=2[CH:3]=1.[H-].[Na+].Br[CH2:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1)=[O:22]>CN(C=O)C>[Cl:16][C:15]1[C:2]([Cl:1])=[CH:3][C:4]2[N:8]([CH2:20][C:21]([C:23]3[CH:24]=[CH:25][C:26]([N+:29]([O-:31])=[O:30])=[CH:27][CH:28]=3)=[O:22])[C:7]([CH2:9][C:10]([F:12])([F:13])[F:11])=[N:6][C:5]=2[CH:14]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 668402-Bromo-4'-nitroacetophenoneHCID 116519105,6-dichloro-2-(2,2,2-trifluoro-ethyl)-1H-benzimidazole

Product 1

HCID 44430229HCID 44430229, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 5,6-dichloro-2-(2,2,2-trifluoro-ethyl)-1H-benzimidazole (304 mg) in DMF (5 mL) was added sodium hydride (68 mg of 60% in oil dispersion). The resulting mixture was stirred at room temperature for 5 min. To the dark green solution was added 2-bromo-4′ nitroacetophenone (348 mg) and the resulting mixture was stirred at room temperature overnight. The reaction mixture was quenched with water, extracted with EtOAc, and dried over Na2SO4. The crude product was purified by silica gel chromatography (10%-40% EtOAc/hexanes) to yield the title compound as an orange colored solid.

Workup

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with EtOAc
  4. dry with materialdried over Na2SO4
  5. customThe crude product was purified by silica gel chromatography (10%-40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-c9f4fd9c68c34f14942e2b3c4d9c4496
Source dataset
uspto-grants-2013_11
Patent number
US08586616B2

Reaction notes

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