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

HRID 1680214Notes

Reaction equation

HRID 1680214 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) is warmed for one hour at 65°. The excess thionyl chloride is removed in vacuo, the residue dissolved in dichloromethane (75 ml) and shaken with excess aqueous potassium carbonate. The organic layer is washed with water, dried over MgSO4, evaporated and the residue evacuated to remove all traces of dichloromethane, affording 1-[2-chloro-4-(4-chlorophenyl)-n-butyl]imidazole.

Workup

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

Sources & evidence

ORD record
ord-816b0b14e1b94841afdf84939a548f3d
Source dataset
uspto-grants-1981_06
Patent number
US04272545

Reaction notes

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