Imidazole → HCID 13013629, compound

HRID 1389782Notes

Reaction equation

HRID 1389782 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]([OH:25])([CH2:23]Cl)[CH2:14][C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[Cl:22])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[NH:28]1[CH:32]=[CH:31][N:30]=[CH:29]1>C(#N)C>[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]([OH:25])([CH2:23][N:28]3[CH:32]=[CH:31][N:30]=[CH:29]3)[CH2:14][C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[Cl:22])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 20295668HCID 20295668, compound

Product 1

HCID 13013629HCID 13013629, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
80 °C

Procedure

A solution of 39.8 g (0.1 mol) of 2-(4-cyclohexylphenyl)-3-chloro-1-(2,4-dichlorophenyl)-propan-2-ol in 200 ml of acetonitrile is added dropwise to a suspension of 3.6 g (0.12 mol) of sodium hydride and 8.2 g (0.12 mol) of imidazole in 200 ml of acetonitrile. After heating the mixture to 80° C. for three hours, it is filtered and the crystal mass is washed with water and recrystallised from acetonitrile. 24.9 g (58% of theory) of 2-(4-cyclohexylphenyl)-1-(2,4-dichlorophenyl)-3-(imidazol-1-yl)-propan-2-ol of melting point 142° C. are obtained.

Workup

  1. filtrationit is filtered
  2. washthe crystal mass is washed with water
  3. customrecrystallised from acetonitrile

Sources & evidence

ORD record
ord-5dbcaa479a8749b4bab5f9d18b8cfd92
Source dataset
uspto-grants-1981_01
Patent number
US04246274

Reaction notes

Loading…