3-Thiocresol → HCID 68488443, compound

HRID 1882339Notes

Reaction equation

HRID 1882339 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[CH3:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:31])[CH:20]=[CH:21]S(C2C=CC=CC=2)(=O)=O)=[CH:14][CH:13]=1.[OH-].[Na+]>CN(C=O)C>[CH3:11][C:12]1[CH:13]=[CH:14][C:15]([NH:18][C:19](=[O:31])[CH:20]=[CH:21][S:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=2)=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 79303-ThiocresolHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 68490534HCID 68490534, compound

Product 1

HCID 68488443HCID 68488443, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 3-methylthiophenol (0.85 g) in DMF (10 mL) was added 60% sodium hydride (81 mg) under a nitrogen atmosphere under ice-cooling. The mixture was stirred at room temperature for 30 minutes under a nitrogen atmosphere, and then was added dropwise to a solution of N-(4-methylphenyl)-3-(phenylsulfonyl)acrylamide (0.85 g) in DMF (10 mL) under ice-cooling. The mixture was stirred at room temperature for 2 hours, alkalinized by addition of a 1N aqueous sodium hydroxide solution, and then extracted with tert-butyl methyl ether (100 mL). The organic layer was washed with water and then a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate=3:1) to obtain N-(4-methylphenyl)-3-(3-methylphenylthio)acrylamide (0.45 g) as a white crystal.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringThe mixture was stirred at room temperature for 2 hours
  4. extractionextracted with tert-butyl methyl ether (100 mL)
  5. washThe organic layer was washed with water
  6. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-98a76a053b004093a13d692b94cccc68
Source dataset
uspto-grants-2012_11
Patent number
US08318981B2

Reaction notes

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