Water → 2-Amino-N-(4-sec-butylphenyl)benzamide
Reaction equation
[CH:1]([C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1)([CH2:3][CH3:4])[CH3:2].[C:12]12[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=1)[NH:17]C(=O)O[C:13]2=[O:14].O>CN(C=O)C>[NH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:12]=1[C:13]([NH:9][C:8]1[CH:7]=[CH:6][C:5]([CH:1]([CH2:3][CH3:4])[CH3:2])=[CH:11][CH:10]=1)=[O:14]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 115 °C
Procedure
4-sec-butyl aniline (B) (1.49 g, 10.0 mmol) was added to a solution of isatoic anhydride (A) (1.63 g, 10.0 mmol) in anhydrous DMF (40 mL) and the reaction mixture was stirred at 115° C. for 16 hours under nitrogen. It was then cooled to room temperature and poured into water (200 mL), and extracted with ethyl acetate (200 mL). The organic phase was washed with water (100 mL), 10% aqueous NaOH solution (100 mL), water (100 mL) and dried over anhydrous Na2SO4. Removal of solvent gave 2-amino-N-(4-sec-butylphenyl)benzamide (C) as a brown solid. Yield: 1.27 g (47%).
Workup
- temperatureIt was then cooled to room temperature
- extractionextracted with ethyl acetate (200 mL)
- washThe organic phase was washed with water (100 mL), 10% aqueous NaOH solution (100 mL), water (100 mL)
- dry with materialdried over anhydrous Na2SO4
- customRemoval of solvent
Sources & evidence
- ORD record
- ord-830ef948f96d4e239f8f412606d83d87
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952021B2
Reaction notes
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