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

HRID 2169009Notes

Reaction equation

HRID 2169009 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-481e1691497a4f258c39ad4deb28c0db
Source dataset
uspto-grants-2015_06
Patent number
US09045436B2

Reaction notes

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