Toluene → HCID 67543919, compound

HRID 1882334Notes

Reaction equation

HRID 1882334 reaction equation
[C:1]1(C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:8]([C:10](=[CH:20][S:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:11]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=O)[CH3:9].[S:28](Cl)(Cl)=O>CN(C=O)C>[CH2:8]([C:10](=[CH:20][S:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:11](=[N:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[S:28][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:9]

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 67543373HCID 67543373, compound

Product 1

HCID 67543919HCID 67543919, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Toluene (20 mL) was added to 2-ethyl-N-phenyl-3-(phenylthio)acrylamide (3.68 g), and then thionyl chloride (1.9 mL) and DMF (10 mg) were added thereto. The mixture was stirred with heating under reflux for 1 hour. The mixture was concentrated under reduced pressure. To the concentrate was added DMF (35 mL), and then, phenylmercaptan sodium salt (2.0 g) was added portionwise thereto under ice-cooling. The mixture was stirred at room temperature for 1 hour. To the reaction mixture was added tert-butyl methyl ether, and then a 1 N aqueous sodium hydroxide solution was added, thereby the solution was separated. The organic layer was washed with water three times, dried and then concentrated. The residue was subjected to silica gel column chromatography (hexane/ethyl acetate=20/1) to obtain phenyl 2-ethyl-N-phenyl-3-(phenylthio)thioacrylimidate (2.03 g).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 1 hour
  3. concentrationThe mixture was concentrated under reduced pressure
  4. additionTo the concentrate was added DMF (35 mL)
  5. additionphenylmercaptan sodium salt (2.0 g) was added portionwise
  6. temperatureunder ice-cooling
  7. stirringThe mixture was stirred at room temperature for 1 hour
  8. additionTo the reaction mixture was added tert-butyl methyl ether
  9. additiona 1 N aqueous sodium hydroxide solution was added
  10. customthe solution was separated
  11. washThe organic layer was washed with water three times
  12. customdried
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-f13153050b664acebd504670f2b95c60
Source dataset
uspto-grants-2012_11
Patent number
US08318981B2

Reaction notes

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