4-(Trifluoromethyl)aniline → alpha-cyano-beta-(4-trifluoromethylanilino)-N-ethoxycarbonylacrylamide

HRID 2198623Notes

Reaction equation

HRID 2198623 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].[F:16][C:17]([F:26])([F:25])[C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1>C(O)C>[C:1]([C:3](=[CH:12][NH:22][C:21]1[CH:23]=[CH:24][C:18]([C:17]([F:25])([F:26])[F:16])=[CH:19][CH:20]=1)[C:4]([NH:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5])#[N:2]

Participants

4

Reactant 2

HCID 99644-(Trifluoromethyl)anilineHCID 230015ethyl N-(2-cyano-3-ethoxyacryloyl)carbamate

Product 1

HCID 70546865alpha-cyano-beta-(4-trifluoromethylanilino)-N-ethoxycarbonylacrylamideYield 90.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of α-cyano-β-ethoxy-N-ethoxycarbonylacrylamide (10 g) and 45 ml of ethanol is heated to affect dissolution. Then 8.12 g of p-trifluoromethylaniline in 10 ml of ethanol is added and the mixture heated at reflux for 45 minutes. The mixture is cooled and filtered to give 14.01 g of α-cyano-β-(4-trifluoromethylanilino)-N-ethoxycarbonylacrylamide, which is added to about 60 ml of tetralin and heated at reflux for several hours. On formation of precipitate, the mixture is allowed to cool and then filtered, washed with ether, to yield 5-cyano-1-(4-trifluoromethylphenyl)uracil, m.p. 230.5°-231.5°.

Workup

  1. temperatureis heated
  2. dissolutiondissolution
  3. temperaturethe mixture heated
  4. temperatureat reflux for 45 minutes
  5. temperatureThe mixture is cooled
  6. filtrationfiltered

Sources & evidence

ORD record
ord-6f8cd172fdc743a3851efddeff9b9866
Source dataset
uspto-grants-1982_11
Patent number
US04358591

Reaction notes

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