Benzoyl chloride → Benzanilide

HRID 749630

Reaction equation

HRID 749630 reaction equation
[C:1]1([NH:7]C2C=CC=CC=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:14](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>N1C=CC=CC=1>[C:14]([NH:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 11487Diphenylamine

Product 1

HCID 7168BenzanilideYield 230.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

830 mg (2.44 mmole) of the aniline compound obtained in step 1 was dissolved in 10 mL of pyridine, 0.340 mL (2.93 mmoles) of benzoylchloride was added, and the mixture was stirred overnight at room temperature. When the reaction had ended, the solvent was removed under reduced pressure. Ethyl acetate and 1N HCl aqueous solution were added to the residue. The mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure, yielding 1.11 g of N-benzoylaniline compound.

Workup

  1. customthe solvent was removed under reduced pressure
  2. additionEthyl acetate and 1N HCl aqueous solution were added to the residue
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe obtained organic layer was washed with saturated brine
  5. dry with materialdried with anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-bd63148fe211469f996a363c66a2399c
Source dataset
uspto-grants-2008_07
Patent number
US07402696B2

Linked notes

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