Benzoyl chloride → N-[2-(4-bromophenylamino)phenyl]benzamide

HRID 2274131Notes

Reaction equation

HRID 2274131 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N+:15]([O-])=O)=[CH:4][CH:3]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)([O-])O.[Na+].[C:31](Cl)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>O1CCCC1.C(OCC)(=O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH:15][C:31](=[O:38])[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 7412Benzoyl chlorideHCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 12000290N-(4-bromophenyl)-2-nitroaniline

Product 1

HCID 23160217N-[2-(4-bromophenylamino)phenyl]benzamideYield 45%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

3.8 g (13 mmol) of (4-bromophenyl)-(2-nitrophenyl)amine was dissolved in 30 mL of tetrahydrofuran. The resulting solution was stirred at room temperature in the argon atmosphere. During the stirring, a solution of 11 g (64 mmol) of sodium hydrosulfite/30 mL of water was added dropwise. After stirring for 5 hours, 20 mL of ethyl acetate was added, and then a solution of 2.2 g (26 mmol) of sodium hydrogen carbonate/20 mL of water was added. Further, a solution of 2.5 g (18 mmol) of benzoyl chloride/10 mL of ethyl acetate was added dropwise, and the resultant was stirred at room temperature for 1 hour. The resultant was extracted with ethyl acetate, and sequentially washed with an aqueous 10% potassium carbonate solution, water and saturated saline. Thereafter, the solution was dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure, whereby 2.1 g (yield 45%) of N-[2-(4-bromophenylamino)phenyl]benzamide was obtained.

Workup

  1. stirringAfter stirring for 5 hours
  2. stirringthe resultant was stirred at room temperature for 1 hour
  3. extractionThe resultant was extracted with ethyl acetate
  4. washsequentially washed with an aqueous 10% potassium carbonate solution, water and saturated saline
  5. dry with materialThereafter, the solution was dried with anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-3864d03fb9634bcb98a7a18f7f4f9295
Source dataset
uspto-grants-2015_09
Patent number
US09126943B2

Reaction notes

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