Imidazole → 1-[2-Hydroxy-2-(2,4-dichlorophenyl)hexyl]imidazole

HRID 1648752Notes

Reaction equation

HRID 1648752 reaction equation
Cl[CH2:2][C:3]([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[Cl:16])([OH:8])[CH2:4][CH2:5][CH2:6][CH3:7].[NH:17]1[CH:21]=[CH:20][N:19]=[CH:18]1.O>CN(C)C=O>[OH:8][C:3]([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[Cl:16])([CH2:4][CH2:5][CH2:6][CH3:7])[CH2:2][N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 962WaterHCID 132368981-Chloro-2-(2,4-dichlorophenyl)hexan-2-ol

Product 1

HCID 130588771-[2-Hydroxy-2-(2,4-dichlorophenyl)hexyl]imidazoleYield 94.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 40 g (0.14 m) of 1-chloro-2-(2,4-dichlorophenyl)hexan-2-ol and 38.6 g (0.57 m) of imidazole in 10 ml of dimethyl formamide is heated at 160° for one hour. The reaction mixture is cooled, poured into 300 ml of water and extracted with ether. The combined ether extracts are washed with water, then saturated sodium chloride solution and dried over MgSO4. Solvent is evaporated to give 42 g of a gummy brown solid, mp 78°-80°.

Workup

  1. temperatureis heated at 160° for one hour
  2. temperatureThe reaction mixture is cooled
  3. extractionextracted with ether
  4. washThe combined ether extracts are washed with water
  5. dry with materialsaturated sodium chloride solution and dried over MgSO4
  6. customSolvent is evaporated

Sources & evidence

ORD record
ord-399e614dc4124a21952f9b8e4eb1c762
Source dataset
uspto-grants-1983_11
Patent number
US04413003

Reaction notes

Loading…