Phosphorus oxychloride → HCID 20251887, compound

HRID 1284490Notes

Reaction equation

HRID 1284490 reaction equation
[NH2:1][C:2]1[C:3]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[N:15]1([CH2:20][C:21](O)=O)[CH:19]=[CH:18][N:17]=[CH:16]1.P(Cl)(Cl)(Cl)=O.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[N:15]1([CH2:20][C:21]2[N:8]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:3]3=[N:4][CH:5]=[CH:6][CH:7]=[C:2]3[N:1]=2)[CH:19]=[CH:18][N:17]=[CH:16]1

Participants

6

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 656129Imidazole-1-acetic acidHCID 106790912-N-phenylpyridine-2,3-diamine

Product 1

HCID 20251887HCID 20251887, compoundYield 26.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3-amino-2-anilinopyridine (2.0 g) and 2-(imidazol-1-yl)acetic acid (1.56 g) in pyridine (20 ml) was dropwise added phosphorus oxychloride (1.91 g) and the mixture was refluxed for 30 minutes. The reaction mixture was poured into saturated aqueous sodium bicarbonate and extracted three times with ethyl acetate. The combined extract was washed with saturated aqueous sodium chloride and dried over magnesium sulfate. The solvent was removed under reduced pressure to give a residue, which was subjected to column chromatography on silica gel (20 g) eluting with a mixture of dichloromethane and ethanol. The fractions containing the desired compound were combined and evaporated in vacuo. The resultant crystal was recrystallized from a mixture of ethyl acetate and n-hexane to give 2-(imidazol-1-yl)methyl-3-phenyl-3H-imidazo[4,5-b]pyridine (0.8 g).

Workup

  1. temperaturethe mixture was refluxed for 30 minutes
  2. extractionextracted three times with ethyl acetate
  3. extractionThe combined extract
  4. washwas washed with saturated aqueous sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customto give a residue, which
  8. washeluting with a mixture of dichloromethane and ethanol
  9. additionThe fractions containing the desired compound
  10. customevaporated in vacuo
  11. customThe resultant crystal was recrystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-fec21570f08a43e193d4ec67ce9b8dd3
Source dataset
uspto-grants-1986_01
Patent number
US04563455

Reaction notes

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