Dimethylformamide → HCID 19385633, compound

HRID 2399444Notes

Reaction equation

HRID 2399444 reaction equation
[CH2:1]([C:5]1[NH:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1)[CH2:2][CH2:3][CH3:4].[H-].[Na+].[CH2:16]([O:23][C:24]1[CH:31]=[CH:30][C:27](CCl)=[CH:26][CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH3:32]N(C=O)C>>[CH2:16]([O:23][C:24]1[CH:31]=[CH:30][C:27]([N:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[C:13]([CH3:32])[C:7]=3[N:6]=[C:5]2[CH2:1][CH2:2][CH2:3][CH3:4])=[CH:26][CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 22122Benzimidazole, 2-butyl-HCID 24758Sodium hydrideHCID 700424-Benzyloxybenzyl chloride

Product 1

HCID 19385633HCID 19385633, compoundYield 96%

Procedure

A suspension of 1.50 g (8.62 mmol) of 2-butylbenzimidazole (described in European Patent Application #400,835, May 12, 1990) and NaH (272 mg, 1.05 eq) in DMF (20 mL) was stirred 25 minutes. Next, 4-benzyloxybenzyl chloride (2.10 g, 1.05 eq) was added to the reaction mixture. After stirring overnight, the reaction mixture was concentrated in vacuo and the residue was chromatographed on a medium pressure liquid chromatograph eluted with 30% ethyl acetate/hexane to yield 3.08 g (96%) of the title compound.

Workup

  1. stirringAfter stirring overnight
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customthe residue was chromatographed on a medium pressure liquid chromatograph
  4. washeluted with 30% ethyl acetate/hexane

Sources & evidence

ORD record
ord-ed078c6fc8924dfe89cec7ab8cd87b40
Source dataset
uspto-grants-1995_09
Patent number
US05449682

Reaction notes

Loading…