Thionyl Chloride → 8-(Chloromethyl)imidazo[1,2-a]pyridine

HRID 1473886Notes

Reaction equation

HRID 1473886 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10]O)[C:5]=12.S(Cl)([Cl:14])=O>>[Cl:14][CH2:10][C:6]1[C:5]2[N:4]([CH:3]=[CH:2][N:1]=2)[CH:9]=[CH:8][CH:7]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 11029987Imidazo[1,2-a]pyridin-8-ylmethanol

Product 1

HCID 216615828-(Chloromethyl)imidazo[1,2-a]pyridine

Conditions

Temperature
75 °C

Procedure

A mixture of imidazo[1,2-a]pyridin-8-ylmethanol (800 mg) and excess thionyl chloride was stirred at 70-80° C. for 8 h. Excess thionyl chloride was removed under vacuum. The residue was then diluted with toluene and evaporated. This procedure was repeated 3 times.

Workup

  1. customExcess thionyl chloride was removed under vacuum
  2. additionThe residue was then diluted with toluene
  3. customevaporated

Sources & evidence

ORD record
ord-76526a3247e240ae85b244aac7857c6b
Source dataset
uspto-grants-2015_04
Patent number
US09018210B2

Reaction notes

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