Diethyl Malonate → N~1~,N~3~-Bis(2,3-dichlorophenyl)propanediamide
Reaction equation
[Cl:1][C:2]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[C:10]([O:18]CC)(=O)[CH2:11][C:12]([O:14]CC)=O>>[Cl:1][C:2]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][C:12](=[O:14])[CH2:11][C:10]([NH:4][C:3]1[CH:5]=[CH:6][CH:7]=[C:8]([Cl:9])[C:2]=1[Cl:1])=[O:18]Participants
3
Conditions
- Temperature
- 170 °C
Procedure
100 mmol 2,3-dichloroaniline and 50 mmol diethyl malonate were put together and stirred at overnight 170° C. The formed ethanol was distilled off directly (100 mmol≡6.6 mL) on a stream of nitrogen. N1,N3-di(2,3-dichloro-phenyl)-malonamide was formed as one solid block. The reaction was cooled and EtOAc was added. The product had to be crushed with a mortar, because it resembled very hard brick. The crushed material was stirred in EtOAc and filtered. EtOAc added was added twice and the mixture was stirred and filtered each time. 14.7 g N1,N3-di(2,3-dichloro-phenyl)-malonamide was obtained (yield 75.0%, purity 98.4%)
Workup
- distillationThe formed ethanol was distilled off directly (100 mmol≡6.6 mL) on a stream of nitrogen
Sources & evidence
- ORD record
- ord-1156273a84fa4620b8fb4317fc18a617
- Source dataset
- uspto-grants-2011_06
- Patent number
- US07964625B2
Reaction notes
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