Triethylamine → 2-[4-(4-Diethylphosphonooxybenzoyl)benzylthio]-3,5-dimethyl-4(3H)-quinazolinone

HRID 1291361Notes

Reaction equation

HRID 1291361 reaction equation
[OH:1][C:2]1[CH:30]=[CH:29][C:5]([C:6]([C:8]2[CH:28]=[CH:27][C:11]([CH2:12][S:13][C:14]3[N:23]([CH3:24])[C:22](=[O:25])[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][C:20]=4[CH3:26])[N:15]=3)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[P:31](Cl)(=[O:38])([O:35][CH2:36][CH3:37])[O:32][CH2:33][CH3:34].C(N(CC)CC)C>O1CCCC1>[CH2:33]([O:32][P:31]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[CH:28]=[CH:27][C:11]([CH2:12][S:13][C:14]3[N:23]([CH3:24])[C:22](=[O:25])[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][C:20]=4[CH3:26])[N:15]=3)=[CH:10][CH:9]=2)=[O:7])=[CH:29][CH:30]=1)([O:35][CH2:36][CH3:37])=[O:38])[CH3:34]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13139Diethyl chlorophosphateHCID 189188882-[4-(4-hydroxybenzoyl)benzylthio]-3,5-dimethyl-4(3H)-quinazolinone

Product 1

HCID 699611962-[4-(4-Diethylphosphonooxybenzoyl)benzylthio]-3,5-dimethyl-4(3H)-quinazolinoneYield 52,693.602%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[4-(4-hydroxybenzoyl)benzylthio]-3,5-dimethyl-4(3H)-quinazolinone (268 mg), diethyl phosphorochloridate (0.16 mg), and triethylamine (0.28 ml) were dissolved in tetrahydrofuran (8 ml) and the solution was stirred at room temperature for 14 hours. This reaction mixture was concentrated and the residue was dissolved in ethyl acetate. The solution was then washed with water, dried, and concentrated, and the residue was crystallized from hexane to provide the title compound as colorless solid (270 mg).

Workup

  1. concentrationThis reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe solution was then washed with water
  4. customdried
  5. concentrationconcentrated
  6. customthe residue was crystallized from hexane

Sources & evidence

ORD record
ord-dc3300df789c4f1f8df6632a302add1e
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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