Aniline → (E)-2-methyl-N-phenyl-3-(phenylthio)-2-propenamide

HRID 2061017Notes

Reaction equation

HRID 2061017 reaction equation
[CH3:1]/[C:2](=[CH:6]\[S:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)/[C:3]([OH:5])=O.S(Cl)(Cl)=O.[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1(C)C=CC=CC=1>[CH3:1]/[C:2](=[CH:6]\[S:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)/[C:3]([NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:5]

Participants

5

Reactant 3

HCID 6115AnilineHCID 24386Thionyl ChlorideHCID 13152781(E)-2-methyl-3-(phenylthio)-2-propenoic acid

Product 1

HCID 59498330(E)-2-methyl-N-phenyl-3-(phenylthio)-2-propenamideYield 87%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 2.5 g (12.8 mmol) of (E)-2-methyl-3-(phenylthio)-2-propenoic acid and 3.5 g (25.7 mmol) of thionyl chloride in 25 ml of toluene was refluxed for 1 hour and then concentrated under vacuum. The residue was dissolved in 25 ml of ethyl acetate and cooled in ice bath. To the solution was added dropwise 2.9 g (32 mmol) of aniline and stirred at room temperature for 30 minutes. The reaction mixture was washed sequentially with 1N HCl solution, a saturated NaHCO3 solution, and a saturated NaCl solution. The organic layer was dried over anhydrous MgSO4 and concentrated to obtain 3.0 g of (E)-2-Methyl-N-phenyl-3-(phenylthio)-2-propenamide.

Workup

  1. temperaturewas refluxed for 1 hour
  2. concentrationconcentrated under vacuum
  3. dissolutionThe residue was dissolved in 25 ml of ethyl acetate
  4. temperaturecooled in ice bath
  5. washThe reaction mixture was washed sequentially with 1N HCl solution
  6. dry with materialThe organic layer was dried over anhydrous MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e063550b00564276b337739f6f0504d9
Source dataset
uspto-grants-2012_10
Patent number
US08278473B2

Reaction notes

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