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

HRID 2061009Notes

Reaction equation

HRID 2061009 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.[Na].[C:27]1([SH:33])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1(C)C=CC=CC=1.CN(C)C=O>[CH3:1][C:2](=[CH:12][S:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:3]([S:33][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[N:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 24819Phosphorus pentachlorideHCID 59498330(E)-2-methyl-N-phenyl-3-(phenylthio)-2-propenamideHCID 66586497Sodium benzenethiol

Product 1

HCID 67543149phenyl 2-methyl-N-phenyl-3-(phenylthio)thioacrylimidateYield 36.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 0.8 g (3 mmol) of (E)-2-methyl-N-phenyl-3-(phenylthio)-2-propenamide in toluene (4 ml) was added 0.62 g (3 mmol) of phosphorus pentachloride and the mixture was stirred at room temperature for 4 hours. After concentration of the mixture under vacuum, the residue was dissolved in 35 ml of N,N-dimethylformamide [DMF] and then 793 mg (6 mmol) of a benzenethiol sodium salt was added portionwise under ice cooling. The mixture was stirred at room temperature for 2 hours. After dilution with tert-butyl methyl ether, the mixture was washed sequentially with water (three times) and saturated NaCl solution, dried over anhydrous MgSO4, and concentrated under vacuum. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/1) to obtain 0.4 g of phenyl 2-methyl-N-phenyl-3-(phenylthio)-2-propenimidothioate (hereinafter referred to as the present compound 1).

Workup

  1. stirringThe mixture was stirred at room temperature for 2 hours
  2. washAfter dilution with tert-butyl methyl ether, the mixture was washed sequentially with water (three times) and saturated NaCl solution
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/1)

Sources & evidence

ORD record
ord-5716523af6894a709898f1277332beef
Source dataset
uspto-grants-2012_10
Patent number
US08278473B2

Reaction notes

Loading…