Dimethylcarbamoyl Chloride → 3,5-Dimethyl-2-[4-[4-(N,N-dimethylcarbamoyloxy)-benzoyl]benzylthio]-4(3H)-quinazolinone

HRID 1291372Notes

Reaction equation

HRID 1291372 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.[CH3:31][N:32]([CH3:36])[C:33](Cl)=[O:34].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:24][N:23]1[C:22](=[O:25])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][C:20]=2[CH3:26])[N:15]=[C:14]1[S:13][CH2:12][C:11]1[CH:27]=[CH:28][C:8]([C:6](=[O:7])[C:5]2[CH:4]=[CH:3][C:2]([O:1][C:33](=[O:34])[N:32]([CH3:36])[CH3:31])=[CH:30][CH:29]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 11430Potassium CarbonateHCID 189188882-[4-(4-hydroxybenzoyl)benzylthio]-3,5-dimethyl-4(3H)-quinazolinone

Product 1

HCID 189190183,5-Dimethyl-2-[4-[4-(N,N-dimethylcarbamoyloxy)-benzoyl]benzylthio]-4(3H)-quinazolinone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-[4-(4-hydroxybenzoyl)benzylthio]-3,5-dimethyl-4(3H)-quinazolinone (478 mg), dimethylcarbamoyl chloride (0.15 ml) and potassium carbonate (315 mg) in DMF (7 ml) was stirred at 50° C. for 48 hours. This reaction mixture was concentrated and the residue was dissolved in ethyl acetate. The solution was washed with water, dried, and concentrated. The residue was recrystallized from ethyl acetate to provide the title compound as colorless solid (346 mg).

Workup

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

Sources & evidence

ORD record
ord-03d71a37215f44438f68b05d0cd266a2
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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