Acetic Acid → 2-[(4-Acetamidophenyl)methylene]-1,3-dicyclopropyl-1,3-propanedione

HRID 486706Notes

Reaction equation

HRID 486706 reaction equation
[C:1]([NH:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[CH:13]1([C:16](=[O:23])[CH2:17][C:18]([CH:20]2[CH2:22][CH2:21]2)=[O:19])[CH2:15][CH2:14]1.N1CCCCC1.C(O)(=O)C>C1(C)C=CC=CC=1>[C:1]([NH:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[C:17]([C:16]([CH:13]2[CH2:15][CH2:14]2)=[O:23])[C:18]([CH:20]2[CH2:22][CH2:21]2)=[O:19])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 739424-AcetamidobenzaldehydeHCID 137807821,3-Dicyclopropylpropane-1,3-dione

Product 1

HCID 190963942-[(4-Acetamidophenyl)methylene]-1,3-dicyclopropyl-1,3-propanedione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture containing 1.6 g 4-acetamidobenzaldehyde, 1.5 g 1,3-dicyclopropyl-1,3-propanedione, 0.2 ml of piperidine and 0.4 ml of acetic acid in 50 ml of toluene was refluxed for 3 h by using a Dean-Stark separator. After standing over night at room temperature the crystals were filtered and washed with toluene. The product was recrystallized from ethanol. Yield 2.0 g, mp 166°-167° C.

Workup

  1. temperaturewas refluxed for 3 h
  2. waitAfter standing over night at room temperature
  3. filtrationthe crystals were filtered
  4. washwashed with toluene
  5. customThe product was recrystallized from ethanol

Sources & evidence

ORD record
ord-b7e1760150024ceb834024b6febd6e5b
Source dataset
uspto-grants-1994_03
Patent number
US05292771

Reaction notes

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