(2,4,6-Trichlorophenyl)hydrazine → alpha-cyano-beta-(2,4,6-trichlorophenylhydrazino)-N-ethoxycarbonylacrylamide

HRID 544194Notes

Reaction equation

HRID 544194 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].[Cl:16][C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[C:18]=1[NH:25][NH2:26]>C(O)C.C1(C)C=CC=CC=1>[C:1]([C:3](=[CH:12][NH:26][NH:25][C:18]1[C:17]([Cl:16])=[CH:22][C:21]([Cl:23])=[CH:20][C:19]=1[Cl:24])[C:4]([NH:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5])#[N:2]

Participants

4

Reactant 2

HCID 79234(2,4,6-Trichlorophenyl)hydrazineHCID 230015ethyl N-(2-cyano-3-ethoxyacryloyl)carbamate

Product 1

HCID 70512904alpha-cyano-beta-(2,4,6-trichlorophenylhydrazino)-N-ethoxycarbonylacrylamide

Reagents, catalysts & solvents 1

HCID 21863594Toluene ethanolSolvent

Procedure

Four grams (18.9 mmol) of α-cyano-β-ethoxy-N-ethoxycarbonylacrylamide is dissolved in hot ethanol/toluene. To this is added, portionwise, 4 g of 2,4,6-trichlorophenylhydrazine. The mixture is heated to reflux for three days. Cooling of the mixture and evaporation of the solvent gives the crude product, which is recrystallized from ethanol (3X) to yield α-cyano-β-(2,4,6-trichlorophenylhydrazino)-N-ethoxycarbonylacrylamide, m.p.=161° (dec.).

Workup

  1. additionTo this is added
  2. temperatureThe mixture is heated
  3. temperatureto reflux for three days
  4. temperatureCooling of the mixture and evaporation of the solvent
  5. customgives the crude product, which
  6. customis recrystallized from ethanol (3X)

Sources & evidence

ORD record
ord-9bb6b37eb2dc4b28a309695713d62952
Source dataset
uspto-grants-1984_05
Patent number
US04448961

Reaction notes

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