O-Toluidine → N,N'-Di-o-tolyl-malonamide

HRID 2425000Notes

Reaction equation

[NH2:1][C:2]1[C:3]([CH3:8])=[CH:4][CH:5]=[CH:6][CH:7]=1.[C:9]([O:17]CC)(=O)[CH2:10][C:11]([O:13]CC)=O>>[CH3:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][C:11](=[O:13])[CH2:10][C:9]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:8])=[O:17]

Participants

Reactant 2

HCID 7242O-Toluidine

HCID 7761Diethyl Malonate

Product 1

HCID 854344N,N'-Di-o-tolyl-malonamide

Conditions

Temperature: 170 °C

Procedure

329 mmol o-toluidine and 165 mmol diethyl malonate were put together and stirred overnight at 170° C. The formed ethanol was distilled off directly on a stream of nitrogen. N1,N3-di(2-methylphenyl)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. 38.1 g N1,N3-di(2-methylphenyl) malonamide (yield 82%) was obtained.

Workup

distillationThe formed ethanol was distilled off directly on a stream of nitrogen

Sources & evidence

ORD record: ord-fb8107454fb54c419e3b9a2e832b77e2
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07964625B2

Reaction notes

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