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

HRID 1918446Notes

Reaction equation

HRID 1918446 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-c1deb334433c4a7dbd43c00886223fde
Source dataset
uspto-grants-2013_12
Patent number
US08618329B2

Reaction notes

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