Hydrochloric Acid → HCID 20026907, compound

HRID 1722605Notes

Reaction equation

HRID 1722605 reaction equation
CC([O-])(C)C.[K+].[C:7]([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:17]([NH2:20])(=[O:19])=[O:18])#[C:8][CH3:9].Cl>CS(C)=O>[CH:7]([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:17]([NH2:20])(=[O:18])=[O:19])=[C:8]=[CH2:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 57072838HCID 57072838, compound

Product 1

HCID 20026907HCID 20026907, compoundYield 15.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4.4 g of potassium tert-butylate are added in portions to a solution of 6.33 g of 2-propynyloxyphenylsulfonamide and 40 ml of dimethyl sulfoxide such that the temperature does not exceed 28° C. The reaction mixture is stirred for 4 hours at 20°-25° C. and, after addition of ice-water, adjusted to pH 7 by the dropwise addition of dilute hydrochloric acid and extracted with ethyl acetate. The organic phase is washed with water and brine, dried over sodium sulfate and concentrated by evaporation. The residue is chromatographed through a column of silica gel to give 1 g of 2-allenyloxyphenylsulfonamide of m.p. 94°-95° C.

Workup

  1. customdoes not exceed 28° C
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated by evaporation
  6. customThe residue is chromatographed through a column of silica gel

Sources & evidence

ORD record
ord-cffa8c84a8da40179978357194491d87
Source dataset
uspto-grants-1989_08
Patent number
US04857100

Reaction notes

Loading…