Acetic Acid → 2-(2,4-Dichlorobenzylidene)-3-oxobutanamide

HRID 1868478Notes

Reaction equation

HRID 1868478 reaction equation
[C:1]([NH2:7])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[Cl:8][C:9]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:10]=1[CH:11]=O.N1CCCCC1.C(O)(=O)C>C(O)(C)C>[Cl:8][C:9]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:10]=1[CH:11]=[C:2]([C:3](=[O:4])[CH3:5])[C:1]([NH2:7])=[O:6]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 134042,4-DichlorobenzaldehydeHCID 80077Acetoacetamide

Product 1

HCID 34229192-(2,4-Dichlorobenzylidene)-3-oxobutanamide

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A suspension of acetoacetamide (5.05 g, 50 mmol), 2,4-di-chlorobenzaldehyde (9.20 g, 52 mmole), piperidine (170 mg, 2 mmol) and acetic acid (120 mg, 2 mmol) in isopropanol (50 mL) was stirred at room temperature for 14 h. The precipitation was collected and rinsed with an additional isopropanol (20 mL). After drying in vacuo, 2-(2,4-dichlorobenzylidene)-3-oxobutanamide was obtained as a white solid (6.3g, 49%).

Workup

  1. customThe precipitation
  2. customwas collected
  3. washrinsed with an additional isopropanol (20 mL)
  4. customAfter drying in vacuo

Sources & evidence

ORD record
ord-0db4162b68bc45ee95007eff1827921c
Source dataset
uspto-grants-2009_12
Patent number
US07635699B2

Reaction notes

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