Benzoic Acid → 4-Bromo-N-(2-(phenylamino)phenyl)benzamide

HRID 2262425Notes

Reaction equation

HRID 2262425 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.C(O)(=O)C1C=CC=CC=1.[C:24]1([NH:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[NH2:37])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C)C=O.O.ClCCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:37][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[NH:30][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[O:8])=[CH:9][CH:10]=1

Participants

8

Reactant 4

HCID 243Benzoic AcidHCID 114644-Bromobenzoic acidHCID 24386Thionyl ChlorideHCID 68297N-Phenyl-o-phenylenediamine

Product 1

HCID 230940554-Bromo-N-(2-(phenylamino)phenyl)benzamideYield 94.4%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

Suspending 3.0 g (15 mmol) of 4-bromobenzoic acid into 30 milliliter of 1,2-dichloroethane, adding 2.7 g (23 mmol) of thionyl chloride and 3 drops of N,N-dimethylformamide, the resultant solution was stirred with heating at the temperature of about 50° C. for 1 hour and 30 minutes until benzoic acid as the material disappeared. After completion of the reaction, removing the solvent and excess thionyl chloride by distillation, dissolving the resultant acid chloride into 30 milliliter of N-methylpyrrolidone, adding 2.8 g (15 mmol) of N-phenyl-1,2-phenylenediamine, the resultant solution was stirred at room temperature for a night. After completion of the reaction, adding water and filtering the precipitated solid, further washing with water and by drying under reduced pressure, 5.2 g of 4-bromo-N-(2-phenylamino-phenyl)-benzamide was obtained.

Workup

  1. customAfter completion of the reaction
  2. customremoving the solvent and excess thionyl chloride
  3. distillationby distillation
  4. dissolutiondissolving the resultant acid chloride into 30 milliliter of N-methylpyrrolidone
  5. customAfter completion of the reaction
  6. filtrationfiltering the precipitated solid
  7. washfurther washing with water
  8. customby drying under reduced pressure

Sources & evidence

ORD record
ord-f6cffc21e0994c5c811ed1e959e055e5
Source dataset
uspto-grants-2010_12
Patent number
US07851071B2

Reaction notes

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