O-Toluidine → alpha-cyano-beta-(2-methylanilino)-N-ethoxycarbonylacrylamide

HRID 2286450Notes

Reaction equation

HRID 2286450 reaction equation
[C:1]([C:3](=[CH:12]OCC)[C:4]([NH:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5])#[N:2].[CH3:16][C:17]1[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=1[NH2:19]>C(O)C>[C:1]([C:3](=[CH:12][NH:19][C:18]1[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=1[CH3:16])[C:4]([NH:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5])#[N:2]

Participants

4

Reactant 2

HCID 7242O-ToluidineHCID 230015ethyl N-(2-cyano-3-ethoxyacryloyl)carbamate

Product 1

HCID 70546834alpha-cyano-beta-(2-methylanilino)-N-ethoxycarbonylacrylamideYield 88.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Ten grams of α-cyano-β-ethoxy-N-ethoxycarbonylacrylamide is dissolved by heating in 50 ml of ethanol to 60°. Then 5.32 g of 2-methylaniline in 20 ml ethanol is added and the mixture heated at reflux for 4 hours with stirring. Crystals appear on cooling and the mixture is filtered and washed with ether to yield 11.36 g of α-cyano-β-(2-methylanilino)-N-ethoxycarbonylacrylamide, which is dissolved in tetralin and heated at reflux for 3 hours. After cooling, the mixture is filtered, washed with ether, to yield 5-cyano-1-(2-methylphenyl)uracil, m.p. 251.5°-2.52.5°.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 4 hours
  3. temperatureon cooling
  4. filtrationthe mixture is filtered
  5. washwashed with ether

Sources & evidence

ORD record
ord-3544e2ca89484faa8e0604fde7ed3d79
Source dataset
uspto-grants-1981_05
Patent number
US04266056

Reaction notes

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