Aniline → Benzanilide

HRID 1577623Notes

Reaction equation

HRID 1577623 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8](Cl)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>ClCCl>[C:8]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 7412Benzoyl chloride

Product 1

HCID 7168BenzanilideYield 73.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzanilide is prepared by the method of Example 5 using 5.0 mls (0.05 mole) of aniline, 7.5 grams of 3A molecular sieves and 7.48 mls (0.064 mole) of benzoyl chloride in 100 mls of dichloromethane. The separated 3A sieves (16.37 g) are extracted with 200 mls of hot 3A alcohol, and the alcohol extract is evaporated to dryness to obtain 7.24 grams (68% of theoretical) of crude benzanilide; m.p. 161°-163° C. after recrystallization from 3A alcohol. Dichloromethane filtrates from above reaction are evaporated to dryness and extracted with ethyl ether to obtain an additional 1.39 grams of crude benzanilide.

Workup

  1. customThe separated 3A sieves (16.37 g)
  2. extractionare extracted with 200 mls of hot 3A alcohol
  3. extractionthe alcohol extract
  4. customis evaporated to dryness

Sources & evidence

ORD record
ord-c77dafe32a2a49dc8b22f0c88e6651d0
Source dataset
uspto-grants-1981_09
Patent number
US04288592

Reaction notes

Loading…