Potassium Hydroxide → HCID 118557960, compound

HRID 2207146Notes

Reaction equation

HRID 2207146 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:7].[OH-].[K+].[CH3:22][C:23]1C=CC(S(OCCC=C)(=O)=O)=[CH:25][CH:24]=1>CS(C)=O.CCOC(C)=O>[CH2:25]([N:8]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:6](=[O:7])[C:5]1[CH:15]=[CH:16][C:17]([O:18][CH3:19])=[C:3]([O:2][CH3:1])[CH:4]=1)[CH2:24][CH:23]=[CH2:22]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 7369543,4-dimethoxy-N-phenylbenzamideHCID 11299102But-3-enyl 4-methylbenzenesulfonate

Product 1

HCID 118557960HCID 118557960, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3,4-dimethoxybenzanilide 33 (771 mg, 3 mmol) and KOH (4 equiv) in DMSO (6 mL) was added but-3-enyl 4-methylbenzenesulfonate (2.85 g, 4 equiv) [prepared as reported in the Journal of the American Chemical Society 2009, 6003] at room temperature and the mixture was heated at 80° C. for 72 h. The mixture was cooled, taken up in EtOAc and washed twice with water. The organic layer was dried over magnesium sulfate, filtered and concentrated to dryness. The residue was purified by column chromatography on SiO2 (gradient of diethylether in petroleum ether) to afford the title compound 34 (Yield 467 mg, 50%).

Workup

  1. customprepared
  2. customat room temperature
  3. temperatureThe mixture was cooled
  4. washwashed twice with water
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe residue was purified by column chromatography on SiO2 (gradient of diethylether in petroleum ether)

Sources & evidence

ORD record
ord-8f5b023b7b9a47cbbfa0ceb5a37f9ce4
Source dataset
uspto-grants-2016_06
Patent number
US09376387B2

Reaction notes

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