Potassium Acetate → HCID 15617368, compound

HRID 1651004Notes

Reaction equation

HRID 1651004 reaction equation
Br[CH2:2][C:3]1[C:4]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:5]([S:9]([NH:12][C:13]([CH3:16])([CH3:15])[CH3:14])(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1.[C:22]([O-:25])(=[O:24])[CH3:23].[K+].C(OCC)(=O)C.CCCCCC>CS(C)=O>[C:22]([O:25][CH2:2][C:3]1[C:4]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:5]([S:9]([NH:12][C:13]([CH3:16])([CH3:15])[CH3:14])(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1)(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 517044Potassium AcetateHCID 15617260HCID 15617260, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 15617368HCID 15617368, compoundYield 54.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 5.0 g of 3-bromomethyl-2-carboethoxy-N-(1,1-dimethylethyl)benzenesulfonamide and 1.5 g of potassium acetate in 50 mL of dimethylsulfoxide was stirred at room temperature for 6 hours. The resulting reaction mixture was poured onto ice and extracted with ethyl acetate. The organic phase was washed with a solution of saturated sodium chloride and then dried over magnesium sulfate. Removal of the drying agent by filtration and concentration provided a white solid. Chromatography on silica gel with 1:1 ethyl acetate/hexane provided 2.58 g of a white solid, m.p. 81°-82° C.

Workup

  1. customThe resulting reaction mixture
  2. additionwas poured onto ice
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with a solution of saturated sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. customRemoval of the drying agent
  7. filtrationby filtration and concentration
  8. customprovided a white solid

Sources & evidence

ORD record
ord-b688fa2870464b448551b90341d7d775
Source dataset
uspto-grants-1990_05
Patent number
US04927453

Reaction notes

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