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

HRID 648158

Reaction equation

HRID 648158 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 (3 X) 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 (3 X)

Sources & evidence

ORD record
ord-d1b32aaa250e4dd1bff5836cad3b6aa9
Source dataset
uspto-grants-1983_10
Patent number
US04411839

Linked notes

Loading…