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

HRID 420460Notes

Reaction equation

HRID 420460 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>C(OCC)(=O)C.O.O1CCCC1>[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

Dissolving 3.8 g (13 mmol) of (4-bromophenyl)-(2-nitrophenyl) amine obtained in the above step (1) into 30 milliliter of tetrahydrofuran, and during agitation under the atmosphere of nitrogen gas and at room temperature, a solution provided by mixing 11 g (64 mmol) of sodium hydrosulfite into 30 milliliter of water was dropped. Subsequently, after stirring for 5 hours, adding 20 milliliter of ethyl acetate and then, a solution provided by mixing 2.2 g (26 mmol) of sodium hydrogen carbonate and 20 milliliter of water was further added. Furthermore, a solution provided by mixing 2.5 g (18 mmol) of benzoyl chloride/10 milliliter of ethyl acetate was dropped and the resultant solution was stirred at room temperature for 1 hour. Extracting the resultant mixture with ethyl acetate, and after sequentially washing with 10% potassium carbonate aqueous solution, with water and with a saturated solution of sodium chloride, it was dried with sulfuric anhydride magnesium, followed by removing the solvent by distillation under reduced pressure, 2.1 g of N-[2-(4-bromophenyl amino)phenyl]benzamide was obtained (yield: 45%).

Workup

  1. customduring agitation under the atmosphere of nitrogen gas and at room temperature, a solution provided
  2. additionwas dropped
  3. customa solution provided
  4. additionwas further added
  5. customFurthermore, a solution provided
  6. additionwas dropped
  7. extractionExtracting the resultant mixture with ethyl acetate
  8. washafter sequentially washing with 10% potassium carbonate aqueous solution, with water and with a saturated solution of sodium chloride, it
  9. dry with materialwas dried with sulfuric anhydride magnesium
  10. customby removing the solvent
  11. distillationby distillation under reduced pressure

Sources & evidence

ORD record
ord-0cb7dcd8d9d942e09b98ff08f491b2a9
Source dataset
uspto-grants-2012_01
Patent number
US08097349B2

Reaction notes

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