Phosphorus oxychloride → 3-Chloromethyl-8-(2-fluorobenzyloxy)-2-methylimidazo[1,2-a]pyridine

HRID 544458Notes

Reaction equation

HRID 544458 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([CH2:16]O)=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1.P(Cl)(Cl)([Cl:24])=O>>[Cl:24][CH2:16][C:12]1[N:8]2[CH:9]=[CH:10][CH:11]=[C:6]([O:5][CH2:4][C:3]3[CH:18]=[CH:19][CH:20]=[CH:21][C:2]=3[F:1])[C:7]2=[N:14][C:13]=1[CH3:15]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 20458963HCID 20458963, compound

Product 1

HCID 204589533-Chloromethyl-8-(2-fluorobenzyloxy)-2-methylimidazo[1,2-a]pyridine

Procedure

A mixture of 8-(2-fluorobenzyloxy)3-hydroxymethyl-2-methyl-imidazo[1,2-a]pyridine from Example 5 (1 g) and phosphorylchloride (15 ml) was heated under reflux for1 hr. Excess phosphorylchloride was distilled off in vacuo, the residue dissolved in hot ethanolic HCL and the mixture filtered to give the title compound as the hydrochloride salt.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for1 hr
  3. distillationExcess phosphorylchloride was distilled off in vacuo
  4. dissolutionthe residue dissolved in hot ethanolic HCL
  5. filtrationthe mixture filtered

Sources & evidence

ORD record
ord-897ce9cb6cf94f23b5992075724e1d19
Source dataset
uspto-grants-1984_05
Patent number
US04450164

Reaction notes

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