Diethyl Malonate → N~1~,N~3~-bis(2,4-dichlorophenyl)malonamide

HRID 424701Notes

Reaction equation

HRID 424701 reaction equation
[C:1]([O:9]CC)(=O)[CH2:2][C:3]([O:5]CC)=O.[Cl:12][C:13]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:14]=1[NH2:15]>>[Cl:12][C:13]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:14]=1[NH:15][C:3](=[O:5])[CH2:2][C:1]([NH:15][C:14]1[CH:16]=[CH:17][C:18]([Cl:20])=[CH:19][C:13]=1[Cl:12])=[O:9]

Participants

3

Reactant 2

HCID 7761Diethyl MalonateHCID 111232,4-Dichloroaniline

Product 1

HCID 3332858N~1~,N~3~-bis(2,4-dichlorophenyl)malonamide

Conditions

Temperature
200 °C

Procedure

A mixture of diethyl malonate (24 g, 0.15 mol) and 2,4-dichloro aniline (60.8 g, 2.5 eq) was heated at 200° C. upon passing nitrogen gas stream to distil out ethanol. Six hours later, the reactants were cooled to room temperature with adding diethylether. The solids produced were filtered and washed with diethylether (yield: 48 g, 82%): 1H NMR (CDCl3) δ10.04 (s, 2H) 8.04 (d, J=9 Hz, 2H) 7.42 (m, 2H) 7.26, (dd, J=2.4, 9 Hz, 2H) 3.74 (s, 2H)

Workup

  1. customto distil out ethanol
  2. temperatureSix hours later, the reactants were cooled to room temperature with adding diethylether
  3. customThe solids produced
  4. filtrationwere filtered
  5. washwashed with diethylether (yield: 48 g, 82%)

Sources & evidence

ORD record
ord-905c8b8d65d24a0e92c193ad2019a0db
Source dataset
uspto-grants-2012_01
Patent number
US08106071B2

Reaction notes

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