Phosphorus pentachloride → phenyl 2-methyl-N-phenyl-3-(phenylthio)thioacrylimidate

HRID 1882333Notes

Reaction equation

HRID 1882333 reaction equation
[CH3:1][C:2](=[CH:12][S:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.P(Cl)(Cl)(Cl)(Cl)Cl>C1(C)C=CC=CC=1>[CH3:1][C:2](=[CH:12][S:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:3](=[N:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[S:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 675446852-methyl-N-phenyl-3-(phenylthio)acrylamide

Product 1

HCID 67543149phenyl 2-methyl-N-phenyl-3-(phenylthio)thioacrylimidateYield 74.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Toluene (4 mL) was added to a mixture of 2-methyl-N-phenyl-3-(phenylthio)acrylamide (0.80 g) and phosphorus pentachloride (0.62 g), and the mixture was stirred at room temperature for 4 hours. The mixture was concentrated under reduced pressure. To the concentrate was added DMF (35 mL), and then, phenylmercaptan sodium salt (793 mg) was added portionwise thereto. The mixture was stirred at room temperature for 2 hours. 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-methyl-N-phenyl-3-(phenylthio)thioacrylimidate (0.4 g).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionTo the concentrate was added DMF (35 mL)
  3. additionphenylmercaptan sodium salt (793 mg) was added portionwise
  4. stirringThe mixture was stirred at room temperature for 2 hours
  5. additionTo the reaction mixture was added tert-butyl methyl ether
  6. additiona 1 N aqueous sodium hydroxide solution was added
  7. customthe solution was separated
  8. washThe organic layer was washed with water three times
  9. customdried
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-9b3ebb374ecd4b7b9d44ff2e9139ee62
Source dataset
uspto-grants-2012_11
Patent number
US08318981B2

Reaction notes

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