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

HRID 544475Notes

Reaction equation

HRID 544475 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([CH2:10]O)=[CH:8][CH:7]=[CH:6][N:5]2[CH:12]=1.S(Cl)([Cl:15])=O>ClCCl>[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([CH2:10][Cl:15])=[CH:8][CH:7]=[CH:6][N:5]2[CH:12]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 139003302-Methylimidazo[1,2-a]pyridine-8-methanol

Product 1

HCID 139003318-(Chloromethyl)-2-methylimidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Methyl-8-hydroxymethylimidazo[1,2-a]pyridine 21.4 g (0.13 mol) is dissolved in 400 ml dichloromethane. To the solution at 0° C. is added dropwise with stirring 19 ml of thionyl chloride. The reaction mixture is stirred for one hour and the dichloromethane is removed under reduced pressure. The residue is dissolved in distilled water, neutralizedat 0° C. with ammonium hydroxide and extracted with dichloromethane.The extracts are combined and dried over anhydrous sodium sulfate. Following filtration, the dichloromethane is removed under reduced pressure to give 2-methyl-8-chloromethylimidazo[1,2-a]pyridine, mp. 110°-112° C.

Workup

  1. additionTo the solution at 0° C. is added dropwise
  2. customthe dichloromethane is removed under reduced pressure
  3. dissolutionThe residue is dissolved in distilled water, neutralizedat 0° C. with ammonium hydroxide
  4. extractionextracted with dichloromethane
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltration
  7. customthe dichloromethane is removed under reduced pressure

Sources & evidence

ORD record
ord-7731897781ef4f7891f1857e8d858771
Source dataset
uspto-grants-1984_05
Patent number
US04450164

Reaction notes

Loading…