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

HRID 1184196Notes

Reaction equation

HRID 1184196 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-acfc1e9d043a447ca87311397d602527
Source dataset
uspto-grants-2014_03
Patent number
US08664380B2

Reaction notes

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