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

HRID 2405453Notes

Reaction equation

HRID 2405453 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.O.C(OCC)(=O)C>[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. A solution of 11 g (64 mmol) of sodium hydrosulfite in 30 mL of water was added dropwise to the solution while stirring the solution at room temperature in an argon atmosphere. After stirring the mixture for 5 hours, 20 mL of ethyl acetate was added to the mixture. A solution of 2.2 g (26 mmol) of sodium hydrogencarbonate in 20 mL of water was then added to the mixture. After the dropwise addition of a solution of 2.5 g (18 mmol) of benzoyl chloride in 10 mL of ethyl acetate, the mixture was stirred at room temperature for 1 hour. The mixture was then extracted with ethyl acetate, washed with water and a saturated sodium chloride solution sequentially, and dried over anhydrous sodium sulfate. The solvent was then evaporated under reduced pressure to obtain 2.1 g of N-[2-(4-bromophenylamino)phenyl]benzamide (yield: 45%).

Workup

  1. stirringAfter stirring the mixture for 5 hours
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. extractionThe mixture was then extracted with ethyl acetate
  4. washwashed with water
  5. dry with materiala saturated sodium chloride solution sequentially, and dried over anhydrous sodium sulfate
  6. customThe solvent was then evaporated under reduced pressure

Sources & evidence

ORD record
ord-9fe67d37f5394597be7cd2fbcafceadf
Source dataset
uspto-grants-2014_08
Patent number
US08803420B2

Reaction notes

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