HCID 15129906, compound → 2-[4-(2-Butylbenzimidazol-1-yl)methylphenyl]benzoic acid

HRID 1655450Notes

Reaction equation

HRID 1655450 reaction equation
[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=3[C:19]([O:21]C)=[O:20])=[CH:13][CH:12]=2)[C:8]2[CH:27]=[CH:28][CH:29]=[CH:30][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4]>[OH-].[Na+].CO>[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]3[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=3[C:19]([OH:21])=[O:20])=[CH:15][CH:16]=2)[C:8]2[CH:27]=[CH:28][CH:29]=[CH:30][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 15129906HCID 15129906, compound

Product 1

HCID 41100262-[4-(2-Butylbenzimidazol-1-yl)methylphenyl]benzoic acidYield 55.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

In a mixture of 1N NaOH solution (4.5 ml) and methanol (10 ml), methyl 2-[4-(2-butylbenzimidazol-1-yl)methylphenyl]benzoate (1.2 g) was heated for 3 hours under reflux. The reaction mixture was concentrated, and the concentrate was dissolved in water, washed with ether, then acidified with 1N-HCl to afford crystals. The crystals were collected by filtration and recrystallized from ethyl acetate - methanol to afford colorless crystals (0.64 g, 53%).

Workup

  1. temperaturewas heated for 3 hours
  2. temperatureunder reflux
  3. concentrationThe reaction mixture was concentrated
  4. dissolutionthe concentrate was dissolved in water
  5. washwashed with ether
  6. customto afford crystals
  7. filtrationThe crystals were collected by filtration
  8. customrecrystallized from ethyl acetate - methanol

Sources & evidence

ORD record
ord-82c9b4a13d104882a9e9f3bcbc02f2b7
Source dataset
uspto-grants-1993_10
Patent number
US05250554

Reaction notes

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