Hydrochloric Acid → 2-Cyclopentyloxypyridin-3-ylsulfonamide

HRID 868179Notes

Reaction equation

HRID 868179 reaction equation
[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

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7298CyclopentanolHCID 24758Sodium hydrideHCID 122344452-chloropyridine-3-sulfonamide

Product 1

HCID 198537212-Cyclopentyloxypyridin-3-ylsulfonamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-8dfab31a5d2a40f884099ec67a58dcf3
Source dataset
uspto-grants-1988_10
Patent number
US04778513

Reaction notes

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