Diethyl Malonate → N~1~,N~3~-bis(3-methylphenyl)malonamide

HRID 2424998Notes

Reaction equation

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

Participants

Reactant 2

HCID 7761Diethyl Malonate

HCID 7934m-Toluidine

Product 1

HCID 679507N~1~,N~3~-bis(3-methylphenyl)malonamide

Conditions

Temperature: 170 °C

Procedure

100 mmol m-toluidine 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-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. 9.5 g N1,N3-di(3-methylphenyl)malonamide (yield 67.3%, purity 97.2%) was obtained.

Workup

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

Sources & evidence

ORD record: ord-3211275a0213488781fb83ef79a3a875
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07964625B2

Reaction notes

Loading…