Phosphorus oxybromide → 4-Bromo-2-(2-ethylsulfanylphenyl)-7-trifluoromethylquinazoline

HRID 521658Notes

Reaction equation

HRID 521658 reaction equation
[CH2:1]([S:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[NH:19][C:18](=O)[C:17]2[C:12](=[CH:13][C:14]([C:21]([F:24])([F:23])[F:22])=[CH:15][CH:16]=2)[N:11]=1)[CH3:2].P(Br)(Br)([Br:27])=O.C(=O)(O)[O-].[Na+]>C(#N)C>[Br:27][C:18]1[C:17]2[C:12](=[CH:13][C:14]([C:21]([F:24])([F:23])[F:22])=[CH:15][CH:16]=2)[N:11]=[C:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[S:3][CH2:1][CH3:2])[N:19]=1

Participants

5

Reactant 3

HCID 24613Phosphorus oxybromideHCID 516892Sodium BicarbonateHCID 1369687532-(2-ethylsulfanylphenyl)-7-trifluoromethyl-3H-quinazolin-4-one

Product 1

HCID 1182058354-Bromo-2-(2-ethylsulfanylphenyl)-7-trifluoromethylquinazolineYield 25.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 500 mg of 2-(2-ethylsulfanylphenyl)-7-trifluoromethyl-3H-quinazolin-4-one, 615 mg of phosphorus oxybromide and 2 ml of acetonitrile was refluxed for 4 hours. A saturated aqueous sodium bicarbonate solution was added to the cooled reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was applied to a silica gel column chromatography to obtain 149 mg of 4-bromo-2-(2-ethylsulfanylphenyl)-7-trifluoromethylquinazoline (Compound of Present Invention 3).

Workup

  1. temperaturewas refluxed for 4 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7f0ca86ebe1d4056b526a1d991077933
Source dataset
uspto-grants-2016_05
Patent number
US09328121B1

Reaction notes

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