Benzenamine, 4-(1-methylpropyl)- → 2-amino-N-(4-sec-butyl-phenyl)-3-methoxy-benzamide

HRID 1846295Notes

Reaction equation

HRID 1846295 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[NH:9]C(=O)O[C:12](=[O:13])[C:7]=2[CH:6]=[CH:5][CH:4]=1.[CH:15]([C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1)([CH2:17][CH3:18])[CH3:16]>CN(C=O)C>[NH2:9][C:8]1[C:3]([O:2][CH3:1])=[CH:4][CH:5]=[CH:6][C:7]=1[C:12]([NH:23][C:22]1[CH:24]=[CH:25][C:19]([CH:15]([CH2:17][CH3:18])[CH3:16])=[CH:20][CH:21]=1)=[O:13]

Participants

4

Reactant 2

HCID 121771Benzenamine, 4-(1-methylpropyl)-HCID 105596798-Methoxy-1H-benzo[d][1,3]oxazine-2,4-dione

Product 1

HCID 866598052-amino-N-(4-sec-butyl-phenyl)-3-methoxy-benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 8-methoxy-1H-benzo[d][1,3]oxazine-2,4-dione (0.50 g, 2.6 mmol) and 4-sec-butylaniline (0.42 g, 2.8 mmol) in DMF (4.0 mL) were stirred at 110° C. under N2 for 24 hours. The mixture was concentrated to dryness then purified by column chromatography on silica gel using ½ EtOAc/hexane as eluent to afford 2-amino-N-(4-sec-butyl-phenyl)-3-methoxy-benzamide as white solid. Yield: 0.533 g (69%).

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. customthen purified by column chromatography on silica gel using ½ EtOAc/hexane as eluent

Sources & evidence

ORD record
ord-c831c3787dee4ebdb2105687684b0532
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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