Aniline → 2-propenamide, 2-methyl-N-((phenylamino)carbonyl)-

HRID 1452126Notes

Reaction equation

HRID 1452126 reaction equation
[C:1]([NH:6][C:7](=[O:11])OCC)(=[O:5])[C:2]([CH3:4])=[CH2:3].[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1(C)C=CC=CC=1>[C:1]([NH:6][C:7]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:11])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

4

Reactant 2

HCID 6115AnilineHCID 13628540Ethyl (2-methylacryloyl)carbamate

Product 1

HCID 2319182-propenamide, 2-methyl-N-((phenylamino)carbonyl)-Yield 45.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

A reaction vessel was charged with 78.5 g of ethyl N-methacryloylcarbamate and 46.5 g of aniline to which 100 g of toluene were added and heated at 120° C. for 30 minutes. The resulting mixture was condensed under reduced pressure and isolated by column chromatography to obtain 46.4 g of N-methacryloyl-N'-phenyl urea having a melting point of 165° to 166° C.

Workup

  1. additionwere added
  2. customcondensed under reduced pressure
  3. customisolated by column chromatography

Sources & evidence

ORD record
ord-59ffe58a053948f3ad86702b888546eb
Source dataset
uspto-grants-1997_02
Patent number
US05606096

Reaction notes

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