Phosphorus oxychloride → 1-Phthalazinamine, N-(2,2-dimethylpropyl)-4-phenyl-

HRID 979465Notes

Reaction equation

HRID 979465 reaction equation
[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=O)[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:18]([NH2:23])[C:19]([CH3:22])([CH3:21])[CH3:20].P(Cl)(Cl)(Cl)=O.C([O-])(O)=O.[Na+]>CC1C=CC(C)=CC=1>[CH2:18]([NH:23][C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:8][N:9]=1)[C:19]([CH3:22])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 79882NeopentylamineHCID 2191504-Phenyl-1-(2H)-phthalazinoneHCID 516892Sodium Bicarbonate

Product 1

HCID 64105951-Phthalazinamine, N-(2,2-dimethylpropyl)-4-phenyl-

Reagents, catalysts & solvents 1

HCID 7809P-XyleneSolvent

Procedure

To a suspension of 100 g of 4-phenyl-1(2H)-phthalazinone and 96.2 g of neopentylamine in 300 ml of p-xylene were added dropwise 83.7 g of phosphorus oxychloride with stirring and the resulting mixture was stirred under reflux for 4 hours. After allowing to be cooled, a saturated aqueous solution of NaHCO3 was added to the reaction mixture. Then, the mixture was extracted with chloroform and the organic layer was separated, dried and then concentrated. The residue was recrystallized from ethanol to afford the title compound as a pale yellow crystal. 100.8 g (Yield, 77%) Melting point: 215.5°-216.5° C.

Workup

  1. stirringthe resulting mixture was stirred
  2. temperatureunder reflux for 4 hours
  3. temperatureto be cooled
  4. extractionThen, the mixture was extracted with chloroform
  5. customthe organic layer was separated
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-52cf5b48f4ad4bf8a41bf72352e89312
Source dataset
uspto-grants-1987_05
Patent number
US04668677

Reaction notes

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