Phosphorus oxychloride → HCID 22292448, compound

HRID 966869Notes

Reaction equation

HRID 966869 reaction equation
P(Cl)(Cl)(Cl)=O.[C:6]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:13][CH:12]=1)(=[O:8])[CH3:7].[C:30]([O-])(=[O:32])C.[Na+]>CN(C=O)C>[C:6]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][C:21]([CH:30]=[O:32])=[CH:20][CH:19]=2)=[CH:13][CH:12]=1)(=[O:8])[CH3:7]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 517045Sodium AcetateHCID 222924294-(N,N-diphenylamino)benzyl acetate

Product 1

HCID 22292448HCID 22292448, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

DMF (2.63 g, 0.036 mol) was added to a three-neck flask (50 mL) equipped with a condenser, CaCl2 drying tube, and a glass stopper and cooled in an ice bath. Phosphorus oxychloride (1.8 g, 0.012 mol) was then added dropwise, and the resulting mixture stirred for 5 minutes and then allowed to warm slowly to room temperature. A solution of 4-(N,N-diphenylamino)benzyl acetate (1.88 g, 0.0059 mol) in DMF (20 mL) was then added dropwise. After addition was complete, the mixture was heated to 70° C. and stirred overnight. The mixture was then poured over ice (20 g) and the product obtained by filtration after slowly neutralizing the solution in an ice bath with saturated sodium acetate solution to pH 6. After washing with deionized water and drying, the product was recrystallized by dissolving in a small quantity of chloroform and pouring into excess hexane to yield the desired product (1.21 g, 60%). m.p. 86-89° C.; 1H NMR δ: 2.12(s, 2H, CH3), 5.09 (s, CH2), 7.0-7.37 (m, 12H, phenyl), 7.65-7.70 (d, 2H, phenyl), 9.81 (s, 1H, CHO). Analysis: Calculated for C22H19NO3: C, 76.52%; H, 5.51%; N, 4.06%. Found: C, 76.27%; H, 5.72%; N, 4.01%.

Workup

  1. customequipped with a condenser, CaCl2 drying tube
  2. temperaturea glass stopper and cooled in an ice bath
  3. additionAfter addition
  4. temperaturethe mixture was heated to 70° C.
  5. stirringstirred overnight
  6. customthe product obtained by filtration
  7. washAfter washing with deionized water
  8. customdrying
  9. customthe product was recrystallized
  10. dissolutionby dissolving in a small quantity of chloroform
  11. additionpouring into excess hexane

Sources & evidence

ORD record
ord-22c882c6d4494b56bf0e933cac0e3e7d
Source dataset
uspto-grants-2005_10
Patent number
US06953570B2

Reaction notes

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