Thionyl Chloride → HCID 22909635, compound

HRID 1379082Notes

Reaction equation

HRID 1379082 reaction equation
[CH2:1]([N:8]1[C:12]([CH3:13])=[C:11]([CH2:14]O)[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=S(Cl)[Cl:18]>C(Cl)(Cl)Cl>[ClH:18].[CH2:1]([N:8]1[C:12]([CH3:13])=[C:11]([CH2:14][Cl:18])[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 13145711HCID 13145711, compound

Product 1

HCID 22909635HCID 22909635, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 1-benzyl-4-hydroxymethyl-5-methylimidazole (0.85 g, 0.0042 mol), prepared according to the method of Ueda et al., BioMed. Chem. Lett., 4:1623, 1994, in CHCl3 (20 ml) at 0° C. was added SOCl2 (0.421 ml, 0.0126 mol). The reaction was refluxed for 3 h, cooled to rt and the solvent removed in vacuo. The resulting solid was rinsed with Et2O (3×10 ml) and dried under vacuum to give 1-benzyl-4-chloromethyl-5-methylimidazole hydrochloride (13) as a white solid; mp 188° C.

Workup

  1. temperatureThe reaction was refluxed for 3 h
  2. customthe solvent removed in vacuo
  3. washThe resulting solid was rinsed with Et2O (3×10 ml)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-6b29273aecd14e0384d32a9685b9bd2c
Source dataset
uspto-grants-1997_09
Patent number
US05670526

Reaction notes

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