Phosphorus oxychloride → HCID 20485151, compound

HRID 647503Notes

Reaction equation

HRID 647503 reaction equation
[C:1]([NH:4][CH2:5][C:6]1[C:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][CH:9]=[CH:8][N:7]=1)(=O)[CH3:2].P(Cl)(Cl)([Cl:22])=O>>[ClH:22].[CH3:2][C:1]1[N:7]2[CH:8]=[CH:9][CH:10]=[C:11]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:6]2=[CH:5][N:4]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 13217542N-{[3-(Benzyloxy)pyridin-2-yl]methyl}acetamide

Product 1

HCID 20485151HCID 20485151, compound

Procedure

Heat under reflux for 0.5 hours a mixture of 5 gms of the compound produced in Example 3 and 75 ml phosphorous oxychloride. Cool the reaction mixture to room temperature and remove the phosphorous oxychloride under reduced pressure. Partition the residue between chloroform and an aqueous solution of sodium bicarbonate. Separate the chloroform layer and dry over potassium carbonate. Filter the resulting dry solution and remove the chloroform from the filtrate under reduced pressure. Chromatograph the residue on silica gel using ethyl acetate-chloroform. Combine the fractions containing the desired product, 3-methyl-8-(phenylmethoxy)imidazo[1,5-a]pyridine and remove the solvent under reduced pressure. Dissolve the resulting solid in absolute ethanol and add an ethanolic hydrogen chloride solution. Remove the ethanol under reduced pressure and recrystallize the residue from acetonitrile to obtain 3-methyl-8-(phenylmethoxy)imidazo[1,5-a]pyridine hydrochloride, mp 174°-175°.

Workup

  1. temperatureHeat
  2. temperatureunder reflux for 0.5 hours
  3. customremove the phosphorous oxychloride under reduced pressure
  4. customPartition the residue between chloroform
  5. customSeparate the chloroform layer
  6. dry with materialdry over potassium carbonate
  7. filtrationFilter the resulting dry solution
  8. customremove the chloroform from the filtrate under reduced pressure
  9. additioncontaining the desired product, 3-methyl-8-(phenylmethoxy)imidazo[1,5-a]pyridine
  10. customremove the solvent under reduced pressure
  11. dissolutionDissolve the resulting solid in absolute ethanol
  12. additionadd an ethanolic hydrogen chloride solution
  13. customRemove the ethanol under reduced pressure
  14. customrecrystallize the residue from acetonitrile

Sources & evidence

ORD record
ord-dffe2c707abc458aa03d2b535744a0bc
Source dataset
uspto-grants-1983_10
Patent number
US04409226

Reaction notes

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