Dichloromethane → 1H-Imidazole-5-methanol, 2-butyl-1-[(2-chlorophenyl)methyl]-

HRID 36970Notes

Reaction equation

HRID 36970 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])[C:7]([CH2:10][O:11]C(=O)C)=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+].C(Cl)Cl>CO>[CH2:1]([C:5]1[N:6]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])[C:7]([CH2:10][OH:11])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 10041718butyl-5-acetoxymethyl-1-(2-chlorophenyl)methyl-1H-imidazole

Product 1

HCID 100164181H-Imidazole-5-methanol, 2-butyl-1-[(2-chlorophenyl)methyl]-Yield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of crude 2-n-butyl-5-acetoxymethyl-1-(2-chlorophenyl)methyl-1H-imidazole (250 g) in methanol (200 mL) was treated with 10% sodium hydroxide solution (700 mL) and the mixture was heated on a steam bath for 4 hours. After cooling, methylene chloride was added, the organic phase was separated, washed with water, dried and concentrated. The residue was dissolved in ether, cooled, and seeded to give the crude product. Recrystallization from ethyl acetate gave 176 g of 2-n-butyl-1-(2-chlorophenyl)methyl-5-hydroxymethyl-1H-imidazole; mp 86°-88° C. This material was identical in all respects to the product prepared by Method 1.

Workup

  1. temperaturethe mixture was heated on a steam bath for 4 hours
  2. temperatureAfter cooling
  3. customthe organic phase was separated
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in ether
  8. temperaturecooled
  9. customto give the crude product
  10. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-3ae0993febb845fe8c83228d0895cdb2
Source dataset
uspto-grants-1995_05
Patent number
US05418250

Reaction notes

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