p-Toluenesulfonic acid → HCID 19707324, compound

HRID 2255264Notes

Reaction equation

HRID 2255264 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]([CH3:12])[C:7](=O)[CH2:6][CH2:5]2.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:25]([NH2:29])(=[O:28])[CH:26]=[CH2:27]>C(OCC)(=O)C.O>[F:1][C:2]1[CH:11]=[CH:10][C:9]2[C:8]3([CH3:12])[C:7](=[CH:6][CH2:5][C:4]=2[CH:3]=1)[NH:29][C:25](=[O:28])[CH2:26][CH2:27]3

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 6579AcrylamideHCID 19707365HCID 19707365, compound

Product 1

HCID 19707324HCID 19707324, compoundYield 17.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 6-fluoro-1-methyl-2-tetralone (7.06 g; 39.6 mmol) in a round bottomed flask was added p-toluenesulfonic acid (1.23 g; 6.5 mmol) and the mixture was stirred at room temperature under nitrogen for 15 minutes. Acrylamide (5.62 g; 79.2 mmol) was added and the reaction mixture was heated to 88°-90° C. under nitrogen for three days. The mixture was diluted with ethyl acetate and water and stirred at room temperature for 1 hour. The resulting layers were separated. The organic layer was washed three times with water, dried over MgSO4 and concentrated to a viscous oil. The crude product was crystallized from ethyl acetate to afford 1.59 g (17% yield) of the subtitle compound. Melting point 202° C.

Workup

  1. temperaturethe reaction mixture was heated to 88°-90° C. under nitrogen for three days
  2. stirringstirred at room temperature for 1 hour
  3. customThe resulting layers were separated
  4. washThe organic layer was washed three times with water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated to a viscous oil
  7. customThe crude product was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-fde485cbf976421dbd22ff509cec16d8
Source dataset
uspto-grants-1993_08
Patent number
US05239075

Reaction notes

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