Dimethyl Sulfoxide → 4-phenyl-6-trifluoromethyl-2(1H)-quinazolinone

HRID 1022406Notes

Reaction equation

HRID 1022406 reaction equation
[C:1]([C:9]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][C:10]=1[NH:11][C:12](=[O:17])C(Cl)(Cl)Cl)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(C)=O.C([O-])(=O)C.[NH4+:34]>O>[C:2]1([C:1]2[C:9]3[C:10](=[CH:18][CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=3)[NH:11][C:12](=[O:17])[N:34]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 517165Ammonium AcetateHCID 124274592'-Benzoyl-2,2,2-trichloro-4'-trifluoromethylacetanilide

Product 1

HCID 124275014-phenyl-6-trifluoromethyl-2(1H)-quinazolinoneYield 100.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 1.08 g of 2′-benzoyl-2,2,2-trichloro-4′-trifluoromethylacetanilide, 10 ml of DMSO and 1.18 g of ammonium acetate was stirred at 75° C. for 1 hour. After cooling, 100 ml of water was added and precipitated crystals were collected by filtration. The resultant collected substance was dissolved in a mixture of hexane:ethyl acetate=1:1, dehydrated using anhydrous magnesium sulfate and then concentrated to obtain 765 mg of the titled compound. 1H NMR (CDCl3): 7.58-7.68 (3H, m), 7.75 (1H, d, J=8.8 Hz), 7.79-7.83 (2H, m), 7.93 (1H, dd, J=8.8, 1.7 Hz), 8.17 (1H, br. s), 13.37 (1H, br. s).

Workup

  1. temperatureAfter cooling
  2. customprecipitated crystals
  3. filtrationwere collected by filtration
  4. customThe resultant collected substance
  5. dissolutionwas dissolved in a mixture of hexane
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c89148645bc942b394aa1a6bd2354251
Source dataset
uspto-grants-2014_05
Patent number
US08722580B2

Reaction notes

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