Phenicarbazide → 1-(beta,beta-Dichloroacryloyl)-1-phenyl-semicarbazide

HRID 127719Notes

Reaction equation

HRID 127719 reaction equation
[C:1]1([NH:7][NH:8][C:9]([NH2:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:12][C:13]([Cl:18])=[CH:14][C:15](Cl)=[O:16]>C(#N)C>[Cl:12][C:13]([Cl:18])=[CH:14][C:15]([N:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[NH:8][C:9]([NH2:11])=[O:10])=[O:16]

Participants

4

Reactant 2

HCID 61002PhenicarbazideHCID 123921313,3-Dichloroprop-2-enoyl chloride

Product 1

HCID 536467151-(beta,beta-Dichloroacryloyl)-1-phenyl-semicarbazideYield 63%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 7 g of 1-phenylsemicarbazide in 100 ml of acetonitrile, cooled down to 0°-5° C., were added 7.4 g of β,β-dichloroacryloyl chloride, under stirring. The addition having been completed, the reaction mixture was stirred at 5° C. for 30 minutes and then at room temperature for 1 (one) hour. The solid that separated was collected by decanting and by filtration, then was washed with diethylether, thus obtaining 8 g of 1-(β,β-dichloroacryloyl)-1-phenyl-semicarbazide, in accordance with the elemental analysis and the I.R. and N.M.R. spectra.

Workup

  1. temperaturecooled down to 0°-5° C.
  2. additionThe addition
  3. stirringthe reaction mixture was stirred at 5° C. for 30 minutes
  4. customat room temperature
  5. customThe solid that separated
  6. customwas collected
  7. customby decanting and by filtration
  8. washwas washed with diethylether

Sources & evidence

ORD record
ord-490f7c74852f44019c3a473b06c7b18d
Source dataset
uspto-grants-1981_03
Patent number
US04256902

Reaction notes

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