Acetanilide → N-[4-(3,4-Dinitrobenzoyl)phenyl]acetamide

HRID 1294077Notes

Reaction equation

HRID 1294077 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[C:7](Cl)=[O:8])([O-:3])=[O:2].[C:16]([NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=[O:18])[CH3:17].[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[C:16]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([C:7]([C:6]2[CH:10]=[CH:11][C:12]([N+:13]([O-:15])=[O:14])=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)=[O:8])=[CH:22][CH:21]=1)(=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 904AcetanilideHCID 6451240Aluminum(III) ChlorideHCID 118064913,4-dinitrobenzoyl Chloride

Product 1

HCID 17755534N-[4-(3,4-Dinitrobenzoyl)phenyl]acetamideYield 6.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 3,4-dinitrobenzoyl chloride (4 mmol), acetoanilide (540 mg, 4 mmol), and AlCl3 (1.6 g) in CH2Cl2 was heated at 40° C. for 24 h. The slurry was washed with HCl (aq) and the product was extracted with ether. It was washed with K2CO3 (aq), dried, and evaporated. Purification by column-chromatography on silica-gel (hexane:AcOEt=1:3) provided 87 mg of the title compound; MS m/e 328 (M−1).

Workup

  1. washThe slurry was washed with HCl (aq)
  2. extractionthe product was extracted with ether
  3. washIt was washed with K2CO3 (aq)
  4. customdried
  5. customevaporated
  6. customPurification by column-chromatography on silica-gel (hexane:AcOEt=1:3)

Sources & evidence

ORD record
ord-4349b20b0a53459590cf7676c88ddd05
Source dataset
uspto-grants-2007_07
Patent number
US07238813B2

Reaction notes

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