2-[4-(2-Butylbenzimidazol-1-yl)methylphenyl]benzoic acid → 2-Butyl-1-[[2'-hydroxymethylbiphenyl-4-yl]methyl]benzimidazole

HRID 1080815Notes

Reaction equation

HRID 1080815 reaction equation
[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23](O)=[O:24])=[CH:13][CH:12]=2)[C:8]2[CH:26]=[CH:27][CH:28]=[CH:29][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4]>C1C=CC=CC=1>[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[CH2:23][OH:24])=[CH:13][CH:12]=2)[C:8]2[CH:26]=[CH:27][CH:28]=[CH:29][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 1

HCID 41100262-[4-(2-Butylbenzimidazol-1-yl)methylphenyl]benzoic acid

Product 1

HCID 545338972-Butyl-1-[[2'-hydroxymethylbiphenyl-4-yl]methyl]benzimidazoleYield 46.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A stirred solution of 2-butyl-1-[(2'-carboxybiphenyl-4-yl)methyl]benzimidazole (1.50 g) in benzene (30 ml) was added dropwise to sodium dihydro-bis(2-methoxyethoxy)aluminate (70% toluene solution). The mixture was stirred for one hour at room temperature, and then heated for 10 minutes under reflux. The reaction mixture was cooled and poured into 2N--HCl, followed by extraction with dichloromethane. The extract was washed with water and dried (MgSO4), and the solvent was evaporated in vacuo. The residue was purified by silica gel (80 g) column chromatography to give the title compound (0.67 g, 46%) as an oil, which was crystallized from ethyl acetate--ether to afford pale yellow prisms, m.p. 162°-163° C.

Workup

  1. temperatureheated for 10 minutes
  2. temperatureunder reflux
  3. temperatureThe reaction mixture was cooled
  4. additionpoured into 2N
  5. extractionHCl, followed by extraction with dichloromethane
  6. washThe extract was washed with water
  7. dry with materialdried (MgSO4)
  8. customthe solvent was evaporated in vacuo
  9. customThe residue was purified by silica gel (80 g) column chromatography

Sources & evidence

ORD record
ord-caa0eafbb71049c68b0e381aae5892d3
Source dataset
uspto-grants-1996_12
Patent number
US05583141

Reaction notes

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