Thionyl Chloride → 1-[2-Chloro-4-(4-chlorophenyl)butyl]-1H-imidazole

HRID 2057943Notes

Reaction equation

HRID 2057943 reaction equation
O[CH:2]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[CH2:3][N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1.S(Cl)([Cl:20])=O>>[Cl:20][CH:2]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[CH2:3][N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 109559944-(4-chlorophenyl)-1-(1H-imidazol-1-yl)-2-butanol

Product 1

HCID 124320341-[2-Chloro-4-(4-chlorophenyl)butyl]-1H-imidazole

Procedure

1-[2-Hydroxy-4-(4-chlorophenyl)-n-butyl]imidazole (2.0 g) in thionyl chloride (10 ml) was warmed for one hour at 65° C. The excess thionyl chloride was removed in vacuo and the residue dissolved in dichloromethane (75 ml) and shaken with excess aqueous potassium carbonate. The organic layer was washed with water, dried (MgSO4), evaporated and the residue evacuated to remove all traces of dichloromethane to afford 1-[2-chloro-4-(4-chlorophenyl)-n-butyl]imidazole.

Workup

  1. customThe excess thionyl chloride was removed in vacuo
  2. dissolutionthe residue dissolved in dichloromethane (75 ml)
  3. washThe organic layer was washed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customthe residue evacuated
  7. customto remove all traces of dichloromethane

Sources & evidence

ORD record
ord-15de986815be4d2b8f0bbf8aa57964e0
Source dataset
uspto-grants-1980_07
Patent number
US04213991

Reaction notes

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