3,4-Dimethylaniline → N~1~,N~3~-Bis(3,4-dimethylphenyl)propanediamide

HRID 2424999Notes

Reaction equation

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

Participants

Reactant 2

HCID 72483,4-Dimethylaniline

HCID 7761Diethyl Malonate

Product 1

HCID 228389N~1~,N~3~-Bis(3,4-dimethylphenyl)propanediamide

Conditions

Temperature: 170 °C

Procedure

100 mmol 3,4-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(3,4-dimethylphenyl)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. 13.9 g N1,N3-di(3,4-dimethylphenyl)malonamide was obtained (yield 89.6%, 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-8baed2f6da654085bbd09a66e2ca5cd3
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07964625B2

Reaction notes

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