4-Acetamidobenzaldehyde → 2-Ethylhexyl 3-(4-acetylaminophenyl)-2-cyanoacrylate

HRID 853725

Reaction equation

HRID 853725 reaction equation
[C:1]([CH2:3][C:4]([O:6][CH2:7][CH:8]([CH2:13][CH3:14])[CH2:9][CH2:10][CH2:11][CH3:12])=[O:5])#[N:2].[C:15]([NH:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1)(=[O:17])[CH3:16]>C(O)(C)C>[C:15]([NH:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=[C:3]([C:1]#[N:2])[C:4]([O:6][CH2:7][CH:8]([CH2:13][CH3:14])[CH2:9][CH2:10][CH2:11][CH3:12])=[O:5])=[CH:21][CH:20]=1)(=[O:17])[CH3:16]

Participants

4

Reactant 2

HCID 739424-AcetamidobenzaldehydeHCID 963592-Ethylhexyl cyanoacetate

Product 1

HCID 692018972-Ethylhexyl 3-(4-acetylaminophenyl)-2-cyanoacrylateYield 54%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 35 g (0.18 mol) of 2-ethylhexyl cyanoacetate and 30 g (0.18 mol) of 4-acetamidobenzaldehyde in 300 ml of isopropanol is refluxed for 3 hours. The reaction mixture is then allowed to cool and is crystallized. The crystals formed are separated out by filtration and are recrystallized from a minimum amount of isopropanol. After filtration and drying, 33.3 g (54% yield) of 2-ethylhexyl 3-(4-acetylaminophenyl)-2-cyanoacrylate are obtained in the form of a pale yellow powder.

Workup

  1. temperatureis refluxed for 3 hours
  2. temperatureto cool
  3. customis crystallized
  4. customThe crystals formed
  5. customare separated out by filtration
  6. customare recrystallized from a minimum amount of isopropanol
  7. filtrationAfter filtration
  8. customdrying

Sources & evidence

ORD record
ord-f8e82cec53444b70b143424e198a23b5
Source dataset
uspto-grants-2007_08
Patent number
US07255853B2

Linked notes

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