Dimethyl malonate → N,N'-bis(4-fluorophenyl)propanediamide

HRID 1694845Notes

Reaction equation

HRID 1694845 reaction equation
[C:1]([O:8]C)(=O)[CH2:2][C:3](OC)=[O:4].[F:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=1>>[F:10][C:11]1[CH:17]=[CH:16][C:14]([NH:15][C:1](=[O:8])[CH2:2][C:3]([NH:15][C:14]2[CH:16]=[CH:17][C:11]([F:10])=[CH:12][CH:13]=2)=[O:4])=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 7943Dimethyl malonateHCID 97314-Fluoroaniline

Product 1

HCID 478246N,N'-bis(4-fluorophenyl)propanediamide

Conditions

Temperature
200 °C

Procedure

A mixture of dimethyl malonate (0.5 g, 3.78 mmol) and 4-fluoroaniline (0.93 g, 8.33 mmol) was heated neat to 200° C. for 20 min in the microwave system. After cooling, the solid was filtered and washed with ethyl acetate to provide the desired malonamide which was used without further purification. MS: Cal'd (MH+) 291, exp (MH+) 291.

Workup

  1. temperatureAfter cooling
  2. filtrationthe solid was filtered
  3. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-9eacd2e019ca4a43a3a2fa53f1a17a40
Source dataset
uspto-grants-2012_04
Patent number
US08158825B2

Reaction notes

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