Thionyl Chloride → 5-(Chloromethyl)imidazo[1,2-a]pyridine hydrochloride

HRID 619417Notes

Reaction equation

HRID 619417 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][C:7]1[N:12]2[CH:13]=[CH:14][N:15]=[C:11]2[CH:10]=[CH:9][CH:8]=1>C(Cl)Cl>[Cl:3][CH2:6][C:7]1[N:12]2[CH:13]=[CH:14][N:15]=[C:11]2[CH:10]=[CH:9][CH:8]=1.[ClH:3]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 11126423{Imidazo[1,2-a]pyridin-5-yl}methanol

Product 1

HCID 211901785-(Chloromethyl)imidazo[1,2-a]pyridine hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution consisting of 58.4 ml (800 mmol) of thionyl chloride and 100 ml of methylene chloride was added 23.68 g (160 mmol) of 5-hydroxymethylimidazo[1,2-a]pyridine with small portions. The reaction mixture was stirred for one hour at room temperature. Then, the solvent and excess amount of thionyl chloride were distilled off under reduced pressure. To the resulting white solid residue was added 100 ml of toluene. The mixture was shaken sufficiently, then the solvent was distilled off under reduced pressure. This process was repeated twice to give 31.85 g (98.0%, white solid) of a crude product.

Workup

  1. distillationThen, the solvent and excess amount of thionyl chloride were distilled off under reduced pressure
  2. additionTo the resulting white solid residue was added 100 ml of toluene
  3. stirringThe mixture was shaken sufficiently
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-bd095d0fdc284603bc56f9d4d900c2dc
Source dataset
uspto-grants-1999_09
Patent number
US05958942

Reaction notes

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