Hydrochloric Acid → 2-Cyclopentyloxypyridin-3-ylsulfonamide

HRID 868179Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 868179
[H-].[Na+].[CH:3]1([OH:8])[CH2:7][CH2:6][CH2:5][CH2:4]1.Cl[C:10]1[C:15]([S:16]([NH2:19])(=[O:18])=[O:17])=[CH:14][CH:13]=[CH:12][N:11]=1.Cl>CN(C)C=O.C(OCC)(=O)C>[CH:3]1([O:8][C:10]2[C:15]([S:16]([NH2:19])(=[O:18])=[O:17])=[CH:14][CH:13]=[CH:12][N:11]=2)[CH2:7][CH2:6][CH2:5][CH2:4]1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 7298CyclopentanolHCID 24758Sodium hydrideHCID 122344452-Chloro-pyridine-3-sulfonic acid amide

Produkt 1

HCID 198537212-Cyclopentyloxypyridin-3-ylsulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

10.9 g of a 55% dispersion of sodium hydride are suspended in 40 ml of dimethylformamide and then 13.6 ml of cyclopentanol are added dropwise. Then a solution of 19.24 g of 2-chloropyridin-3-ylsulfonamide in 40 ml of dimethylformamide is added dropwise and the reaction mixture is stirred for 2 hours at 35°-40° C. and then taken up in a mixture of 250 ml of ethyl acetate, 250 ml of ice-water and 125 ml of 1N hydrochloric acid. After extraction with 3×100 ml of ethyl acetate the combined organic phases are washed with 4×100 ml of water. The organic solution is washed and dried, affording an oily residue which crystallises after trituration with 50 ml of ether to give 19.64 g of 2-cyclopentyloxypyridin-3-ylsulfonamide with a melting point of 134°-135° C.

Aufarbeitung

  1. extractionAfter extraction with 3×100 ml of ethyl acetate the combined organic phases
  2. washare washed with 4×100 ml of water
  3. washThe organic solution is washed
  4. customdried
  5. customaffording an oily residue which
  6. customcrystallises after trituration with 50 ml of ether

Quellen und Nachweise

ORD-Eintrag
ord-8dfab31a5d2a40f884099ec67a58dcf3
Quelldatensatz
uspto-grants-1988_10
Patentnummer
US04778513

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