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

HRID 848698Notes

Reaction equation

HRID 848698 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 effect 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-87ec9cf3b80f4dda893b00e06c9fd81d
Source dataset
uspto-grants-1981_10
Patent number
US04297297

Reaction notes

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