Isatoic Anhydride → HCID 10564674, compound

HRID 1846287Notes

Reaction equation

HRID 1846287 reaction equation
[NH:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4](=[O:11])OC1=O.[F:13][C:14]([F:23])([F:22])[C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1>CN(C=O)C.C(OCC)(=O)C>[NH2:1][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[C:4]([NH:19][C:18]1[CH:20]=[CH:21][C:15]([C:14]([F:13])([F:22])[F:23])=[CH:16][CH:17]=1)=[O:11]

Participants

5

Reactant 2

HCID 8359Isatoic AnhydrideHCID 99644-(Trifluoromethyl)aniline

Product 1

HCID 10564674HCID 10564674, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
115 °C

Procedure

To a solution of 1H-benzo[d][1,3]oxazine-2,4-dione (1.63 g, 10.0 mmol) in anhydrous DMF (20 mL) was added 4-trifluoromethyl-aniline (1.61 g, 10.0 mmol) and the reaction mixture was stirred at 115° C. for 16 hours. It was then cooled to room temperature, diluted with ethyl acetate (150 mL), and the organic phase was washed with water (100 mL), 10% aq. NaOH solution (100 mL), water (150 mL), brine (150 mL), and dried over anhydrous Na2SO4. Solvent was evaporated and the crude compound was purified by the Simpliflash system (20% ethyl acetate in hexanes as eluent) to give 2-amino-N-(4-trifluoromethyl-phenyl)-benzamide as an off-white solid. Yield: 0.2 g (7%).

Workup

  1. temperatureIt was then cooled to room temperature
  2. washthe organic phase was washed with water (100 mL), 10% aq. NaOH solution (100 mL), water (150 mL), brine (150 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. customSolvent was evaporated
  5. customthe crude compound was purified by the Simpliflash system (20% ethyl acetate in hexanes as eluent)

Sources & evidence

ORD record
ord-945911710cd3422592bffb0ea315e5a1
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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