Water → Benzamide, N-(2-benzoylphenyl)-

HRID 1983222Notes

Reaction equation

HRID 1983222 reaction equation
[C:1]1([C:7]2[O:8][C:9](=[O:17])[C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O>C(Cl)Cl.C1COCC1>[C:9]([C:10]1[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=1[NH:12][C:7](=[O:8])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:17])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 962WaterHCID 13926Bentranil

Product 1

HCID 207331Benzamide, N-(2-benzoylphenyl)-Yield 60%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-phenyl-benzo[d][1,3]oxazin-4-one (5 mmol) in dry CH2Cl2 (20 mL) was added 1N solution of aryl magnesium bromide in THF (5 mL) at 0° C. The mixture was stirred at room temperature for 2 h and poured into water (30 mL). The aqueous layer was extracted with ethyl acetate (3×30 mL) and was washed with water (3×50 mL), brine (1×50 mL), dried (anhydrous Na2SO4) and concentrated in vacuo to afford N-(2-benzoyl-phenyl)-benzamide in 60-70% yield.

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate (3×30 mL)
  2. washwas washed with water (3×50 mL), brine (1×50 mL)
  3. dry with materialdried (anhydrous Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1ebc0b8b6538433f8f996382591fe99f
Source dataset
uspto-grants-2009_06
Patent number
US07541373B2

Reaction notes

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