Phosphorus oxychloride → HCID 18983871, compound

HRID 1440475Notes

Reaction equation

HRID 1440475 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]3[C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=[CH:11][N:10]3[CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:19][C:20]1[CH:21]=[C:22]([CH:26]([NH2:29])[C:27]#[N:28])[CH:23]=[CH:24][CH:25]=1.C([O-])(O)=O.[Na+].P(Cl)(Cl)(Cl)=O>C(#N)C>[C:1]1([C:7]2[N:8]=[C:9]3[C:14]([C:15]([NH:29][CH:26]([C:22]4[CH:23]=[CH:24][CH:25]=[C:20]([Cl:19])[CH:21]=4)[C:27]#[N:28])=[O:17])=[CH:13][CH:12]=[CH:11][N:10]3[CH:18]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 112064732-amino-2-(3-chlorophenyl)acetonitrileHCID 221476312-Phenylimidazo[1,2-a]pyridine-8-carboxylic acid

Product 1

HCID 18983871HCID 18983871, compoundYield 27.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-phenyl-imidazo[1,2-a]pyridine-8-carboxylic acid (1.0 g, 4.2 m moles), α-(3-chlorophenyl)-aminoacetonitrile (0.77 g, 4.6 m moles) and NaHCO3 (1.1 g, 13.1 m moles) were added to acetonitrile 110 ml). Phosphorus oxychloride (0.7 ml, 7.51 m moles, dissolved in 5 ml of acetonitrile) was added slowly to the mixture with stirring under ice-cooling. The mixture was reacted at room temperature for 10 hours, and the solvent was removed from the reaction mixture under reduced pressure. Water (50 ml) was added to the residue and the mixture was adjusted to pH 7 with saturated aqueous solution of sodium bicarbonate and then extracted with dichloromethane/ethyl acetate (10/1) (100 ml×2). The extract was dried over anhydrous magnesium sulfate and concentrated. Acetonitrile (5 ml) was added to the concentrate, and the precipitating crystals were collected by filtration to give the object compound (0.44 g, yield 27.2%) as crystals. m.p. 210°-211° C.

Workup

  1. temperaturecooling
  2. customThe mixture was reacted at room temperature for 10 hours
  3. customthe solvent was removed from the reaction mixture under reduced pressure
  4. additionWater (50 ml) was added to the residue
  5. extractionextracted with dichloromethane/ethyl acetate (10/1) (100 ml×2)
  6. dry with materialThe extract was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. additionAcetonitrile (5 ml) was added to the concentrate
  9. filtrationthe precipitating crystals were collected by filtration

Sources & evidence

ORD record
ord-3559e048b5df4b90b7c170f5899f3bc5
Source dataset
uspto-grants-1996_03
Patent number
US05498774

Reaction notes

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