Potassium Carbonate → HCID 15603002, compound

HRID 1272359Notes

Reaction equation

HRID 1272359 reaction equation
[C:1]1(/[C:7](/[CH3:13])=[CH:8]/[S:9]([NH2:12])(=[O:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:20][C:21]1[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:22]=1[C:23](Cl)=[O:24]>O1CCOCC1>[Cl:20][C:21]1[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:22]=1[C:23]([NH:12][S:9](/[CH:8]=[C:7](/[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)\[CH3:13])(=[O:10])=[O:11])=[O:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 666452,4-Dichlorobenzoyl chlorideHCID 15150092HCID 15150092, compound

Product 1

HCID 15603002HCID 15603002, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

(E)-2-Phenyl-propene-1-sulfonic acid amide is dissolved in dioxane followed by the addition of potassium carbonate and 2,4-dichlorobenzoyl chloride. The resulting solution is stirred in a sealed tube at 100° C. for 18.5 h, cooled to room temperature (RT) and partitioned between 1M HCl and ethyl acetate. The aqueous phase is separated and extracted with further portions of ethyl acetate. The organic fractions are combined, washed with brine, dried over MgSO4 and concentrated in vacuo. After flash column chromatography (dichloromethane) (E)-2-phenyl-propene-1-sulfonic acid 2,4-dichlorobenzoylamide can be isolated as a colourless oil. Yield 90 mg (80%).

Workup

  1. temperaturecooled to room temperature (RT)
  2. custompartitioned between 1M HCl and ethyl acetate
  3. customThe aqueous phase is separated
  4. extractionextracted with further portions of ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ded41b0c791d495ab0a0193541fb74bd
Source dataset
uspto-grants-2007_04
Patent number
US07208526B2

Reaction notes

Loading…