Imidazole → Ethyl 2-(4-fluorophenylcarbamoyl)-3-methylbut-2-enoate

HRID 1662024

Reaction equation

HRID 1662024 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[C:9](=[C:12]([C:18](OCC)=[O:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14])([CH3:11])[CH3:10].N1C=CN=C1>CCOC(C)=O>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:18]([C:12](=[C:9]([CH3:10])[CH3:11])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:19])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 97314-FluoroanilineHCID 81255Diethyl isopropylidenemalonate

Product 1

HCID 66767015Ethyl 2-(4-fluorophenylcarbamoyl)-3-methylbut-2-enoateYield 39%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
200 °C

Procedure

To a solution of 4-fluoroaniline (2 g, 18 mmol) in diethyl isopropylidenemalonate (10 g, 50 mmol) is added 1H-imidazole (0.25 g, 3.67 mmol). The reaction mixture is stirred at 200° C. under N2 for 3 hours. After the reaction is cooled, silica gel is added. The mixture is loaded onto a silica gel column, and eluted first with PE and then PE:EtOAc (3:1) to give the product (1.85 g, 39% yield). MS (m/z): 266.1 (M+H).

Workup

  1. temperatureAfter the reaction is cooled
  2. additionsilica gel is added
  3. washeluted first with PE

Sources & evidence

ORD record
ord-93ee3a44f7fd409fb10f6c02f3b7b135
Source dataset
uspto-grants-2011_10
Patent number
US08030302B2

Linked notes

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