Phosphorus oxychloride → 3-Benzyl-2,4-dichloro-1,3-dihydroimidazo[4,5-c]pyridine

HRID 501443Notes

Reaction equation

HRID 501443 reaction equation
P(Cl)(Cl)(Cl)=O.P(Cl)(Cl)(Cl)(Cl)[Cl:7].[CH2:12]([N:19]1[C:23]2[C:24]([Cl:28])=[N:25][CH:26]=[CH:27][C:22]=2[NH:21][C:20]1=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[CH2:12]([N:19]1[C:23]2[C:24]([Cl:28])=[N:25][CH:26]=[CH:27][C:22]=2[NH:21][CH:20]1[Cl:7])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 230705823-Benzyl-4-chloro-1,3-dihydroimidazo[4,5-c]pyridin-2-one

Product 1

HCID 574728443-Benzyl-2,4-dichloro-1,3-dihydroimidazo[4,5-c]pyridineYield 31.5%

Procedure

5 ml of phosphorus oxychloride and 0.338 g of phosphorus pentachloride were added to 0.383 g of 3-benzyl-4-chloro-1,3-dihydroimidazo[4,5-c]pyridin-2-one, and the mixture was heated under reflux for 24 hours. The solvent was concentrated under reduced pressure, and the residue was poured into 50 g of ice/water. The mixture was extracted with 100 ml of ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography. Thus, 0.13 g of the title compound was obtained from the fraction eluted with ethyl acetate-hexane (2:1).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 24 hours
  3. concentrationThe solvent was concentrated under reduced pressure
  4. additionthe residue was poured into 50 g of ice/water
  5. extractionThe mixture was extracted with 100 ml of ethyl acetate
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-53dbd2e5180a424786f7c844bb04039b
Source dataset
uspto-grants-2010_08
Patent number
US07772226B2

Reaction notes

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