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

HRID 642995Notes

Reaction equation

HRID 642995 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([CH2:13]O)[N:10]=[CH:9]2)=[CH:4][CH:3]=1.O=S(Cl)[Cl:17]>>[Cl:17][CH2:13][C:11]1[N:10]=[CH:9][N:8]([C:5]2[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=2)[CH:12]=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 9.3 (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)-1H-imidazole 9.5 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-baf734acf10e40b6abb1e70a858932ba
Source dataset
uspto-grants-2010_04
Patent number
US07696352B2

Reaction notes

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