Thionyl Chloride → 4-Chloromethyl 1-(4-iodophenyl)imidazole

HRID 559519Notes

Reaction equation

HRID 559519 reaction equation
O[CH2:2][C:3]1[N:4]=[CH:5][N:6]([C:8]2[CH:13]=[CH:12][C:11]([I:14])=[CH:10][CH:9]=2)[CH:7]=1.O=S(Cl)[Cl:17]>>[Cl:17][CH2:2][C:3]1[N:4]=[CH:5][N:6]([C:8]2[CH:13]=[CH:12][C:11]([I:14])=[CH:10][CH:9]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 592601064-Hydroxymethyl 1-(4-iodophenyl)imidazole

Product 1

HCID 592600624-Chloromethyl 1-(4-iodophenyl)imidazole

Procedure

The compound 4-hydroxymethyl 1-(4-iodophenyl)imidazole I-1 (0.810 g, 2.70 mmol) was dissolved in SOCl2 (6 mL). The solution was stirred at room temperature for 15 min. It was then concentrated in vacuo. The residue was partitioned between EtOAc and 5% aq. NaHCO3. The organic layer was separated, dried over Na2SO4, concentrated in vacuo to give 4-chloromethyl 1-(4-iodophenyl)imidazole 1-3 as a solid (0.780 g). MS 318.9 and 320.9 (M+H, Cl pattern).

Workup

  1. concentrationIt was then concentrated in vacuo
  2. customThe residue was partitioned between EtOAc and 5% aq. NaHCO3
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6fc9c8a63d1f4806bf43eee621f8d82c
Source dataset
uspto-grants-2011_11
Patent number
US08063077B2

Reaction notes

Loading…