Benzenamine, 4-(1-methylpropyl)- → HCID 86659804, compound

HRID 1846293Notes

Reaction equation

HRID 1846293 reaction equation
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[NH:7]C(=O)O[C:10](=[O:11])[C:5]=2[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>[NH2:7][C:6]1[CH:13]=[CH:14][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[C:10]([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:11]

Participants

4

Reactant 2

HCID 121771Benzenamine, 4-(1-methylpropyl)-HCID 2944796-methoxy-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

Product 1

HCID 86659804HCID 86659804, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
115 °C

Procedure

To a flask (100 mL) with magnetic stirrer was added 6-methoxy-1H-benzo[d][1,3]oxazine-2,4-dione (1.55 g, 8.00 mmol), 4-sec-butylaniline (1.19 mL, 8.0 mmol) and anhydrous DMF (10 mL). The reaction mixture was stirred at 115° C. for 16 hours under nitrogen. DMF was removed and the residue was mixed with water (100 mL) and ethyl acetate (150 mL). The organic phase was separated and washed with brine (50 mL). The solvent was removed and the residue was purified by column chromatography on silica gel (230-400 mesh) using hexane/ethyl acetate=1:1 to give 2-amino-N-(4-sec-butyl-phenyl)-5-methoxy-benzamide. Yield: 0.90 g (37%).

Workup

  1. customDMF was removed
  2. additionthe residue was mixed with water (100 mL) and ethyl acetate (150 mL)
  3. customThe organic phase was separated
  4. washwashed with brine (50 mL)
  5. customThe solvent was removed
  6. customthe residue was purified by column chromatography on silica gel (230-400 mesh)

Sources & evidence

ORD record
ord-bef54f4a9d0140c283abbd23f94f16f6
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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