Aluminum(III) Chloride → 4'-[(2-(3-Methylbutyl)-5-hydroxy-6-methoxy-benzimidazol-1-yl)-methyl]biphenyl-2-carboxylic acid

HRID 344143

Reaction equation

HRID 344143 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[CH3:5][CH:6]([CH3:38])[CH2:7][CH2:8][C:9]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[C:22]([C:27]([OH:29])=[O:28])=[CH:23][CH:24]=[CH:25][CH:26]=3)=[CH:17][CH:16]=2)[C:12]2[CH:30]=[C:31]([O:36][CH3:37])[C:32]([O:34]C)=[CH:33][C:11]=2[N:10]=1>ClCCl>[CH3:5][CH:6]([CH3:38])[CH2:7][CH2:8][C:9]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[C:22]([C:27]([OH:29])=[O:28])=[CH:23][CH:24]=[CH:25][CH:26]=3)=[CH:17][CH:16]=2)[C:12]2[CH:30]=[C:31]([O:36][CH3:37])[C:32]([OH:34])=[CH:33][C:11]=2[N:10]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 150693604'-[(2-(3-Methylbutyl)-5,6-dimethoxy-benzimidazol-1-yl)-methyl]biphenyl-2-carboxylic acid

Product 1

HCID 150693884'-[(2-(3-Methylbutyl)-5-hydroxy-6-methoxy-benzimidazol-1-yl)-methyl]biphenyl-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3 g of aluminium trichloride are added to a suspension of 600 mg (1.3 mmol) of 4'-[(2-(3-methylbutyl)-5,6-dimethoxy-benzimidazol-1-yl)-methyl]biphenyl-2-carboxylic acid in 50 ml of dry dichloromethane and the mixture is heated under reflux for 15 minutes. The solvent is then distilled off, the residue is filtered off under suction, washed using 30 ml of water and dried. 360 mg (62% of theoretical) of a mixture of the isomeric products is obtained after chromatographing over silica gel (eluting agent: dichloromethane/ethanol=9:1).

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 15 minutes
  3. distillationThe solvent is then distilled off
  4. filtrationthe residue is filtered off under suction
  5. washwashed
  6. customdried
  7. addition360 mg (62% of theoretical) of a mixture of the isomeric products
  8. customis obtained after chromatographing over silica gel (eluting agent: dichloromethane/ethanol=9:1)

Sources & evidence

ORD record
ord-ab3b77ca0d30432a9ebac45cccfa1e26
Source dataset
uspto-grants-1999_01
Patent number
US05864043

Linked notes

Loading…