Diethyl Malonate → N,N'-Bis-(3-chloro-phenyl)-malonamide

HRID 522370Notes

Reaction equation

HRID 522370 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[C:9]([O:17]CC)(=O)[CH2:10][C:11]([O:13]CC)=O>C(OCC)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][C:11](=[O:13])[CH2:10][C:9]([NH:5][C:4]2[CH:6]=[CH:7][CH:8]=[C:2]([Cl:1])[CH:3]=2)=[O:17])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 7761Diethyl MalonateHCID 79323-Chloroaniline

Product 1

HCID 458048N,N'-Bis-(3-chloro-phenyl)-malonamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
220 °C

Procedure

3-chloroaniline (5.01 g) and diethyl malonate (2.51 ml) were combined in a flask and heated to 220° C. utilizing a short path condenser with nitrogen bleed over the reaction to remove reaction ethanol. The reaction was stirred for 18 hours and then cooled to room temperature. The solid that had formed in the flask was broken up in diethyl ether 30 mL to give free flowing orange solid upon filtration and washing with ether (3.75 g). LRMS (ES+) m/z (M+H)+ 322.9.

Workup

  1. custombleed over the reaction
  2. customto remove
  3. customreaction ethanol
  4. temperaturecooled to room temperature
  5. customThe solid that had formed in the flask
  6. customto give free
  7. filtrationupon filtration
  8. washwashing with ether (3.75 g)

Sources & evidence

ORD record
ord-660cbca93268498c8614f0069621faf9
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

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