Thionyl Chloride → 2-(chloromethyl)-5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole

HRID 83921Notes

Reaction equation

HRID 83921 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([C:12]2[N:16]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[C:15]([CH2:24]O)=[N:14][CH:13]=2)([CH3:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[Cl:8].S(Cl)([Cl:28])=O>CC#N>[Cl:28][CH2:24][C:15]1[N:16]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[C:12]([C:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)([CH3:11])[CH3:10])=[CH:13][N:14]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 66740712(5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-yl)methanol

Product 1

HCID 667400042-(chloromethyl)-5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-yl)methanol (402 mg, 1.06 mmol) in CH3CN (6 mL) at 0° C. was added thionyl chloride. After stirring 3 h, the solution was concentrated under reduced pressure, and azeotroped with DCM (3×) to give 2-(chloromethyl)-5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole as a yellow solid (420 mg) that was used directly for the next step without purification.

Workup

  1. concentrationthe solution was concentrated under reduced pressure
  2. customazeotroped with DCM (3×)

Sources & evidence

ORD record
ord-f426fb3005914a8d95f4637db78276f6
Source dataset
uspto-grants-2014_09
Patent number
US08846739B2

Reaction notes

Loading…