2,5-Dimethylaniline → HCID 2786260, compound

HRID 2424995Notes

Reaction equation

[CH3:1][C:2]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:3]=1[NH2:4].[C:10]([O:18]CC)(=O)[CH2:11][C:12]([O:14]CC)=O>>[CH3:1][C:2]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:3]=1[NH:4][C:12](=[O:14])[CH2:11][C:10]([NH:4][C:3]1[CH:5]=[C:6]([CH3:9])[CH:7]=[CH:8][C:2]=1[CH3:1])=[O:18]

Participants

Reactant 2

HCID 72592,5-Dimethylaniline

HCID 7761Diethyl Malonate

Product 1

HCID 2786260HCID 2786260, compound

Conditions

Temperature: 170 °C

Procedure

100 mmol 2,5-dimethylaniline and 50 mmol diethyl malonate were put together and stirred overnight at 170° C. The formed ethanol was distilled off directly (100 mmol,≡6.6 mL) on a stream of nitrogen. N1,N3-di(2,5-dimethyl-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. 14.9 g N1,N3-di(2,5-dimethyl-phenyl)-malonamide was obtained (yield 96.0%, purity 98.5%)

Workup

distillationThe formed ethanol was distilled off directly (100 mmol,≡6.6 mL) on a stream of nitrogen

Sources & evidence

ORD record: ord-d117811f195f45058a1391ab67fa2a1f
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07964625B2

Reaction notes

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