N-phenyl-3-(phenylthio)acrylamide → HCID 86617324, compound

HRID 661740Notes

Reaction equation

HRID 661740 reaction equation
[C:1]1([NH:7][C:8](=[O:18])[CH:9]=[CH:10][S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:19]([O+](CC)CC)[CH3:20].F[B-](F)(F)F.[H+].ClCCl>C(Cl)(Cl)Cl>[C:1]1([N:7]=[C:8]([O:18][CH2:19][CH3:20])[CH:9]=[CH:10][S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 68865691N-phenyl-3-(phenylthio)acrylamideHCID 86617325HCID 86617325, compound

Product 1

HCID 86617324HCID 86617324, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

N-phenyl-3-(phenylthio)acrylamide (2.0 g) was dissolved to chloroform (10 ml), and 7.8 ml of tetrafluoroboric acid triethyloxonium-dichloromethane 1 mol/L solution was added thereto dropwise under ice-cooling. It was stirred for one hour at room temperature, 50° C. for two hours and for five hours under heat refluxing. After cooling, ice-water was added to the reaction solution, then the chloroform layer was separated. The chloroform layer was washed with water, dried and distilled off the solvent. The residue was subjected to silica gel column chromatography (hexane/ethyl acetate=15/1) to obtain ethyl N-phenyl-3-(phenylthio)acrylimidate (0.15 g) as oil.

Workup

  1. additionwas added
  2. temperaturedropwise under ice-cooling
  3. temperatureunder heat
  4. temperaturerefluxing
  5. temperatureAfter cooling
  6. customthe chloroform layer was separated
  7. washThe chloroform layer was washed with water
  8. customdried
  9. distillationdistilled off the solvent

Sources & evidence

ORD record
ord-b92e2b72d7fe4408af22a6fb6ebd6be9
Source dataset
uspto-grants-2011_12
Patent number
US08084644B2

Reaction notes

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