Dimethylformamide → HCID 68490140, compound

HRID 1882335Notes

Reaction equation

HRID 1882335 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:30])[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]([O:30][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:21]=[CH:22][S:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=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 68490140HCID 68490140, compoundYield 164.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

Thionyl chloride (1.53 mL) and DMF (catalytic amount) were added to a solution of N-(5-indanyl)-3-(phenylthio)acrylamide (2.47 g) in toluene (80 mL), and the mixture was stirred at 70° C. for 1 hour. The reaction mixture was concentrated under reduced pressure. To the residue was added anhydrous THF (40 mL). To a solution of phenol (1.18 g) in anhydrous THF (20 mL) was added sodium hydride (60%) (0.769 g) under a nitrogen atmosphere under ice-cooling, and then stirred at room temperature under a nitrogen atmosphere for 30 minutes. The reaction mixture was added to the above-described reaction mixture under ice-cooling, and the mixture was stirred at room temperature for 2.5 hours. To the reaction mixture was added ethyl acetate (200 mL), which was washed with a 1N aqueous sodium hydroxide solution, water and then a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was isolated and purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to obtain phenyl N-(5-indanyl)-3-(phenylthio)acrylimidate (2.56 g) as a orange oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionTo the residue was added anhydrous THF (40 mL)
  3. additionTo a solution of phenol (1.18 g) in anhydrous THF (20 mL) was added sodium hydride (60%) (0.769 g) under a nitrogen atmosphere under ice-
  4. temperaturecooling
  5. stirringstirred at room temperature under a nitrogen atmosphere for 30 minutes
  6. additionThe reaction mixture was added to the above-described reaction mixture under ice-
  7. temperaturecooling
  8. stirringthe mixture was stirred at room temperature for 2.5 hours
  9. additionTo the reaction mixture was added ethyl acetate (200 mL), which
  10. washwas washed with a 1N aqueous sodium hydroxide solution, water
  11. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  12. concentrationconcentrated under reduced pressure
  13. customThe residue was isolated
  14. custompurified by silica gel column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-0dfba28f9cfa45e4940bfa6564c81ee9
Source dataset
uspto-grants-2012_11
Patent number
US08318981B2

Reaction notes

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