Phenylacetic Acid → Benzeneacetamide, N-(2-acetylphenyl)-

HRID 364925

Reaction equation

HRID 364925 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].[C:11]1([CH2:17][C:18](O)=[O:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[C:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][C:18](=[O:19])[CH2:17][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 999Phenylacetic AcidHCID 10868DicyclohexylcarbodiimideHCID 110862'-Aminoacetophenone

Product 1

HCID 218938Benzeneacetamide, N-(2-acetylphenyl)-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of o-aminoacetophenone (25 g.) and phenylacetic acid (25 g.) in anhydrous methylene dichloride (200 ml.) was prepared. To that mixture was added dicyclohexylcarbodiimide (40 g.) in portions of approx. 10 g. every 5 min. at ambient temperature. When the addition was completed the mixture was stirred for 4 hr. at ambient temperature. The mixture was then filtered, and the filtrate was evaporated in vacuo to dryness. The residue was crystallised from cyclohexane to give o-acetyl-N-(phenylacetyl)aniline, m.p. 78°.

Workup

  1. customwas prepared
  2. customevery 5 min.
  3. customat ambient temperature
  4. additionWhen the addition
  5. customat ambient temperature
  6. filtrationThe mixture was then filtered
  7. customthe filtrate was evaporated in vacuo to dryness
  8. customThe residue was crystallised from cyclohexane

Sources & evidence

ORD record
ord-c30de0092d444a9b9d4cc6dd5c8c2e66
Source dataset
uspto-grants-1986_08
Patent number
US04607039

Linked notes

Loading…