Sodium hydride → HCID 44430181, compound

HRID 2043261Notes

Reaction equation

HRID 2043261 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+].[N+:19]([C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Br)=[CH:24][CH:23]=1)([O-:21])=[O:20]>CN(C=O)C>[Cl:16][C:15]1[C:2]([Cl:1])=[CH:3][C:4]2[N:8]([CH2:26][C:25]3[CH:28]=[CH:29][C:22]([N+:19]([O-:21])=[O:20])=[CH:23][CH:24]=3)[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 660114-Nitrobenzyl bromideHCID 116519105,6-dichloro-2-(2,2,2-trifluoro-ethyl)-1H-benzimidazole

Product 1

HCID 44430181HCID 44430181, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 5,6-dichloro-2-(2,2,2-trifluoro-ethyl)-1H-benzimidazole (355 mg) in DMF (5 mL) was added sodium hydride (110 mg of 60% in oil) and 4-nitrobenzyl bromide (596 mg). 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 a light orange solid.

Workup

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

Sources & evidence

ORD record
ord-8de2472a1a5e4d25bfc6bcf888b9422c
Source dataset
uspto-grants-2013_11
Patent number
US08586616B2

Reaction notes

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