Thionyl Chloride → Ethyl 3-(chloromethyl)imidazo[1,2-a]pyridine-2-carboxylate hydrochloride

HRID 1509529Notes

Reaction equation

HRID 1509529 reaction equation
O[CH2:2][C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]2=[N:5][C:4]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13].S(Cl)([Cl:19])=O>C(Cl)(Cl)Cl>[ClH:19].[Cl:19][CH2:2][C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]2=[N:5][C:4]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 18466901Ethyl 3-(hydroxymethyl)imidazo[1,2-a]pyridine-2-carboxylate

Product 1

HCID 67320957Ethyl 3-(chloromethyl)imidazo[1,2-a]pyridine-2-carboxylate hydrochloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of ethyl 3-(hydroxymethyl)imidazo[1,2-a]pyridine-2-carboxylate (2.85 g) in chloroform (40 ml) was added thionyl chloride (8.0 ml) at room temperature, and the mixture was heated under reflux for 12 hr. The reaction solution was cooled to room temperature, and concentrated under reduced pressure. The precipitated crystals were collected by filtration, washed with diethyl ether to give the object product (3.50 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 12 hr
  3. concentrationconcentrated under reduced pressure
  4. filtrationThe precipitated crystals were collected by filtration
  5. washwashed with diethyl ether

Sources & evidence

ORD record
ord-0aa06fbf3d0b4de7b6d2d36624b69d27
Source dataset
uspto-grants-2015_12
Patent number
US09221836B2

Reaction notes

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