Dimethylformamide → HCID 68491182, compound

HRID 1882332Notes

Reaction equation

HRID 1882332 reaction equation
S(Cl)(Cl)=O.CN(C=O)C.[CH2:10]1[C:18]2[C:13](=[CH:14][C:15]([NH:19][C:20](=O)[CH:21]=[CH:22][S:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:16][CH:17]=2)[CH2:12][CH2:11]1>C1(C)C=CC=CC=1>[CH2:10]1[C:18]2[C:13](=[CH:14][C:15]([N:19]=[C:20]([S:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:21]=[CH:22][S:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:16][CH:17]=2)[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 68489916HCID 68489916, compound

Product 1

HCID 68491182HCID 68491182, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

Thionyl chloride (0.75 mL) and DMF (catalytic amount) were added to a solution of N-(5-indanyl)-3(phenylthio)acrylamide (1.21 g) in toluene (50 mL) at room temperature, and the mixture was stirred at 70° C. for 2 hours. The reaction mixture was concentrated under reduced pressure. To the residue was added THF (40 mL), and then a solution (0.62 mol/L, 10 mL) of phenylmercaptan sodium salt in THF was added thereto under ice-cooling. The mixture was stirred at room temperature for 2 hours, and then alkalilized by addition of a 1N aqueous sodium hydroxide solution, followed by extraction with ethyl acetate (250 mL). The organic layer was washed with water and then a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate=100:1 to 50:1) to obtain phenyl N-(5-indanyl)-3-(phenylthio)thioacrylimidate (Z-isomer: 0.27 g, E-isomer: 0.94 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionTo the residue was added THF (40 mL)
  3. additiona solution (0.62 mol/L, 10 mL) of phenylmercaptan sodium salt in THF was added
  4. temperatureunder ice-cooling
  5. stirringThe mixture was stirred at room temperature for 2 hours
  6. additionalkalilized by addition of a 1N aqueous sodium hydroxide solution
  7. extractionfollowed by extraction with ethyl acetate (250 mL)
  8. washThe organic layer was washed with water
  9. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3038f3fb804440578c26f40433092110
Source dataset
uspto-grants-2012_11
Patent number
US08318981B2

Reaction notes

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