Thionyl Chloride → 2-Chloromethyl-imidazo(1,2-A)pyridine

HRID 334549Notes

Reaction equation

HRID 334549 reaction equation
O[CH2:2][C:3]1[N:4]=[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][N:6]2[CH:11]=1.S(Cl)([Cl:14])=O>C(Cl)Cl>[Cl:14][CH2:2][C:3]1[N:4]=[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][N:6]2[CH:11]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 2795540Imidazo[1,2-a]pyridin-2-ylmethanol

Product 1

HCID 9576142-Chloromethyl-imidazo(1,2-A)pyridineYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a round bottomed flask containing 2-hydroxymethyl-imidazo[1,2-a]pyridine (800 mg, 5.4 mmol) in DCM (8 mL), was added at R.T. thionyl chloride (1.96 mL, 27 mmol). The solution became clear and 10 min later, a precipitated was formed. The reaction mixture was stirred at R.T. for 2 hours and the solvent was removed under reduced pressure to afford 1.10 g of a brownish solid as the chlorhydrate form of 2-(chloromethyl)-imidazo[1,2-a]pyridine (Yield: 100%).

Workup

  1. customlater, a precipitated was formed
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-63ab32d84f3e40a4bb7f9d061ea77442
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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