Phosphorus oxychloride → HCID 178432152, compound

HRID 2181023Notes

Reaction equation

HRID 2181023 reaction equation
[CH3:1][C:2]1[NH:12][C:5]2=[N+:6]([O-])[CH:7]=[CH:8][C:9]([CH3:10])=[C:4]2[N:3]=1.P(Cl)(Cl)([Cl:15])=O>C(Cl)(Cl)Cl>[Cl:15][C:7]1[N:6]=[C:5]2[NH:12][C:2]([CH3:1])=[N:3][C:4]2=[C:9]([CH3:10])[CH:8]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178432172HCID 178432172, compound

Product 1

HCID 178432152HCID 178432152, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2,7-dimethyl-3H-imidazo[4,5-b]pyridine-4-oxide (4.45 g), chloroform (4.5 ml) and phosphorus oxychloride (25.4 ml) was stirred at 80° C. for 3 hr and concentrated to dryness under reduced pressure. The residue was poured into ice (75 g) and neutralized with aqueous ammonia under ice-cooling. After stirring at room temperature for 30 min, the precipitated solid was collected by filtration and washed with water to give 5-chloro-2,7-dimethyl-3H-imidazo[4,5-b]pyridine as a gray powder (3.66 g).

Workup

  1. concentrationconcentrated to dryness under reduced pressure
  2. additionThe residue was poured into ice (75 g)
  3. temperaturecooling
  4. stirringAfter stirring at room temperature for 30 min
  5. filtrationthe precipitated solid was collected by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-ca67efb649c54053b2de1c875db7c973
Source dataset
uspto-grants-2005_05
Patent number
US06890934B2

Reaction notes

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