Acetyl chloride → N-(5-bromo-2-nitrophenyl)acetamide

HRID 1966439Notes

Reaction equation

HRID 1966439 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:8])[CH:7]=1.[C:12](Cl)(=[O:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH:8][C:12](=[O:14])[CH3:13])[CH:7]=1

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 11430Potassium CarbonateHCID 53147665-Bromo-2-nitroaniline

Product 1

HCID 3368439N-(5-bromo-2-nitrophenyl)acetamideYield 70%

Procedure

A solution of 5-bromo-2-nitrobenzenamine (0.5 g, 2.3 mmol), acetyl chloride (0.18 ml, 2.5 mmol) and potassium carbonate (0.64 g, 4.6 mmol) was stirred at 0° C. for 2 hours. The mixture was washed with water (2×10 ml) and dried over anhydrous sodium sulfate before removing the solvents. Crude N-(5-bromo-2-nitrophenyl)acetamide (0.40 g, 70%) was obtained after removing of the solvents. A solution of N-(5-bromo-2-nitrophenyl)acetamide (0.3 g, 1.1 mmol) and benzoyl piperazine (0.44 g, 2.3 mml) was stirred at 105° C. under argon atmosphere for 16 hours. The reaction was quenched with 500 ml water and extracted with ethyl acetate (2×10 ml). N-(5-(4-benzoylpiperazin-1-yl)-2-nitrophenyl)acetamide (0.4 g, 93%) was obtained after flash column chromatograph (50% ethyl acetate in hexanes). 1H NMR (500 MHz, CDCl3) δ (ppm) 2.31 (s, 3H), 3.40-3.57 (m, 8H), 6.56 (dd, J=2.8, 9.7 Hz, 1H), 7.48 (m, 5H), 8.21 (d, J=9.7 Hz, 1H), 8.38 (d, J=9.7 Hz, 1H), 11.0 (s, 1H). 13C NMR (125 MHz, CDCl3): δ (ppm) 26.4, 47.1, 47.3, 61.4, 103.8, 108.5, 127.2, 127.6, 129.0, 129.1, 130.7, 135.5, 138.3, 155.7, 170.1, 171.1

Workup

  1. washThe mixture was washed with water (2×10 ml)
  2. dry with materialdried over anhydrous sodium sulfate
  3. custombefore removing the solvents

Sources & evidence

ORD record
ord-d143fc7a01624779a64b116074159bf6
Source dataset
uspto-grants-2013_04
Patent number
US08420640B2

Reaction notes

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