Hydrochloric Acid → HCID 16750549, compound

HRID 908087Notes

Reaction equation

HRID 908087 reaction equation
[C:1]([C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[S:11]([NH:14][CH2:15][CH3:16])(=[O:13])=[O:12])#[N:2].C(=O)([O-])[O-].[K+].[K+].Cl>O1CCOCC1.O>[CH2:15]([N:14]1[C:1](=[NH:2])[C:3]2[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=2[S:11]1(=[O:13])=[O:12])[CH3:16]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 49800663HCID 49800663, compound

Product 1

HCID 16750549HCID 16750549, compoundYield 55.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

1.50 g (6.24 mmol) 2-Cyano-N-ethyl-3-methoxy-benzenesulfonamide were added to a solution of 2.59 g (18.7 mmol) potassium carbonate in a mixture of 15 ml 1,4 dioxane and 6 ml of water. The solution was stirred for 24 h at room temperature. The solution was neutralized by addition of 10% HCl (pH=7). The solution was extracted twice with ethyl acetate. The organic layers were dried over Na2SO4 and concentrated. The crude product which still contained starting material was dissolved in a mixture of ethyl acetate and 10% HCl and vigorously shaken. The layers were separated and the aqueous layer was neutralized by addition of sodium bicarbonate. The aqueous layer was extracted twice with ethyl acetate. The organic layers were dried over Na2SO4 and concentrated to yield 830 mg (3.45 mmol) of the title compound having a melting point (Tmp) of 111-114° C.

Workup

  1. extractionThe solution was extracted twice with ethyl acetate
  2. dry with materialThe organic layers were dried over Na2SO4
  3. concentrationconcentrated
  4. dissolutionwas dissolved in a mixture of ethyl acetate and 10% HCl
  5. stirringvigorously shaken
  6. customThe layers were separated
  7. additionthe aqueous layer was neutralized by addition of sodium bicarbonate
  8. extractionThe aqueous layer was extracted twice with ethyl acetate
  9. dry with materialThe organic layers were dried over Na2SO4
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-b13f568a3d764c6cb7b84e056aee1794
Source dataset
uspto-grants-2011_09
Patent number
US08017554B2

Reaction notes

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