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

HRID 1802573Notes

Reaction equation

HRID 1802573 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-f6efa2b1c979463dbf5ee97f35acd8b8
Source dataset
uspto-grants-2013_01
Patent number
US08349873B2

Reaction notes

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