Acetone → Benzanilide

HRID 258332

Reaction equation

HRID 258332 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.CC(C)=O.Cl>O>[C:2]1([NH:1][C:8](=[O:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 180Acetone2×HCID 313Hydrochloric AcidHCID 6115Aniline2×HCID 7412Benzoyl chloride2×

Product 1

HCID 7168Benzanilide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-phenylbenzamide (Structure II) is synthesized from aniline and benzoyl chloride using acetone as a reaction media and an aqueous solution of NAOH to neutralize the HCl generated. A 20 ml aqueous solution of NAOH (2.57 grams, 0.064 moles) and 6.0 grams (0.064 moles) of aniline are first added to a stirred 250 ml flask containing 75 ml of acetone. Benzoyl chloride (9.06 grams, 0.064 moles) is next added over a five minute period. This reaction mixture which now contains a white precipitate is stirred for 1.5 hours and then diluted with 50 ml of deionized water. This solution is next filtered and the filter cake obtained is sequentially washed with 50 ml of deionized water (two times) followed by 50 ml of methanol. The washed filter cake is recovered and DSC analysis of this product showed a sharp melting endotherm at 169° C. ##STR10##

Workup

  1. customas a reaction media
  2. filtrationnext filtered
  3. customthe filter cake obtained
  4. washis sequentially washed with 50 ml of deionized water (two times)
  5. filtrationThe washed filter cake
  6. customis recovered
  7. customat 169° C.

Sources & evidence

ORD record
ord-917b214182fe44ee870caf62af832cef
Source dataset
uspto-grants-1993_11
Patent number
US05266661

Linked notes

Loading…