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

HRID 1636424Notes

Reaction equation

HRID 1636424 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 separtaed, 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 indentical 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. washwashed with water
  4. customdried
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in ether
  7. temperaturecooled
  8. customto give the crude product
  9. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-333e647201d54539a24ec3169f496e98
Source dataset
uspto-grants-2000_03
Patent number
US06034114

Reaction notes

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