2,6-Difluoroaniline → alpha-cyano-beta-(2,6-difluoroanilino)-N-ethoxycarbonylacrylamide

HRID 2286441Notes

Reaction equation

HRID 2286441 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]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:18]=1[NH2:19]>C(O)C>[C:1]([C:3](=[CH:12][NH:19][C:18]1[C:17]([F:16])=[CH:23][CH:22]=[CH:21][C:20]=1[F:24])[C:4]([NH:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5])#[N:2]

Participants

4

Reactant 2

HCID 796472,6-DifluoroanilineHCID 230015ethyl N-(2-cyano-3-ethoxyacryloyl)carbamate

Product 1

HCID 70547626alpha-cyano-beta-(2,6-difluoroanilino)-N-ethoxycarbonylacrylamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To 10.0 g of α-cyano-β-ethoxy-N-ethoxycarbonylacrylamide dissolved in about 40 ml of hot ethanol is added 6.45 g of 2,6-difluoroaniline in 15 ml of ethanol. The reaction mixture is stirred at reflux for about 6 hours, cooled and filtered to yield α-cyano-β-(2,6-difluoroanilino)-N-ethoxycarbonylacrylamide, white solid (12.61 g), which is added to 60 ml of tetralin and heated at reflux for 5 hours. The mixture is allowed to cool, filtered and washed with ether to yield 10.21 g of 5-cyano-1-(2,6-difluorophenyl)uracil, white solid.

Workup

  1. temperatureat reflux for about 6 hours
  2. temperaturecooled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-e8d1e9eb78ce46f889b855c56d1499a8
Source dataset
uspto-grants-1981_05
Patent number
US04266056

Reaction notes

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