3-(4-Benzenesulfonylaminophenyl)-N-hydroxyacrylamide → HCID 18618656, compound

HRID 2402425Notes

Reaction equation

HRID 2402425 reaction equation
ONC(=O)C=CC1C=C[C:9]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:15])=[O:14])=CC=1.C([O-])([O-])=O.[K+].[K+].[CH3:29][I:30]>CN(C=O)C>[CH3:9][NH:12][S:13]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=1[C:16]1[CH:21]=[CH:20][C:29]([I:30])=[CH:18][CH:17]=1)(=[O:14])=[O:15]

Participants

5

Reactant 3

HCID 41513-(4-Benzenesulfonylaminophenyl)-N-hydroxyacrylamideHCID 6328Methyl iodideHCID 11430Potassium Carbonate

Product 1

HCID 18618656HCID 18618656, compoundYield 196.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To compound 28 (from Example 18) (500 mg, 1.39 mmol) in DMF (10 mL) were added at room temperature K2CO3 (962 mg, 6.96 mmol), followed by methyl iodide (395 mg, 2.78 mmol). The resulting reaction mixture was stirred at room temperature for 16 hours. The solvent is then removed and water was added. The resulting mixture was extracted with ethyl acetate, and the combined organic phases were dried and concentrated. Purification by flash chromatography using hexane:ethyl acetate (8:2) afforded 510 mg (98%) of the title compound as a white solid.

Workup

  1. customThe resulting reaction mixture
  2. customThe solvent is then removed
  3. additionwater was added
  4. extractionThe resulting mixture was extracted with ethyl acetate
  5. customthe combined organic phases were dried
  6. concentrationconcentrated
  7. customPurification by flash chromatography

Sources & evidence

ORD record
ord-0f6511b511e54d32bcb9998bc278f0ab
Source dataset
uspto-grants-2014_08
Patent number
US08796330B2

Reaction notes

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