Benzenamine, 4-(1-methylpropyl)- → HCID 67461929, compound

HRID 1846290Notes

Reaction equation

HRID 1846290 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]2[C:13](=[O:14])OC(=O)[NH:10][C:9]=2[CH:16]=1)(=[O:4])=[O:3].[CH:17]([C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1)([CH2:19][CH3:20])[CH3:18]>CN(C)C=O.O>[NH2:10][C:9]1[CH:16]=[C:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH:6]=[CH:7][C:8]=1[C:13]([NH:25][C:24]1[CH:26]=[CH:27][C:21]([CH:17]([CH2:19][CH3:20])[CH3:18])=[CH:22][CH:23]=1)=[O:14]

Participants

5

Reactant 2

HCID 121771Benzenamine, 4-(1-methylpropyl)-HCID 86659803HCID 86659803, compound

Product 1

HCID 67461929HCID 67461929, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 7-methanesulfonyl-1H-benzo[d][1,3]oxazine-2,4-dione (0.98 g, 3.8 mmol) and 4-sec-butylaniline (0.57 g, 3.8 mmol) in N,N-dimethylformamide (30 mL) was stirred at 115° C. for 16 hours, cooled to room temperature, diluted with water (50 mL), extracted with ethyl acetate (2×100 mL), and concentrated using a rotary evaporator. The residue was further purified by column chromatography (SiO2, hexane/ethyl acetate=2:1) to provide 2-amino-N-(4-sec-butyl-phenyl)-4-methanesulfonyl-benzamide. Yield: 0.466 g (33%).

Workup

  1. extractionextracted with ethyl acetate (2×100 mL)
  2. concentrationconcentrated
  3. customa rotary evaporator
  4. customThe residue was further purified by column chromatography (SiO2, hexane/ethyl acetate=2:1)

Sources & evidence

ORD record
ord-1ab112e83b2f4d2389558c959407916f
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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