Hydrochloric Acid → 2-Cyclopropylmethoxypyridin-3-ylsulfonamide

HRID 868181Notes

Reaction equation

HRID 868181 reaction equation
[H-].[Na+].[CH:3]1([CH2:6][OH:7])[CH2:5][CH2:4]1.Cl[C:9]1[C:14]([S:15]([NH2:18])(=[O:17])=[O:16])=[CH:13][CH:12]=[CH:11][N:10]=1.Cl>CN(C)C=O.C(OCC)(=O)C>[CH:3]1([CH2:6][O:7][C:9]2[C:14]([S:15]([NH2:18])(=[O:17])=[O:16])=[CH:13][CH:12]=[CH:11][N:10]=2)[CH2:5][CH2:4]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 75644CyclopropanemethanolHCID 122344452-chloropyridine-3-sulfonamide

Product 1

HCID 198537232-Cyclopropylmethoxypyridin-3-ylsulfonamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

11.99 g of a 55% dispersion of sodium hydride are suspended in 40 ml of dimethylformamide and 13.04 ml of cyclopropylmethanol are added dropwise at 10° C. under a nitrogen atmosphere. The mixture is stirred for 15 minutes and then a solution of 21.16 g of 2-chloropyridin-3-ylsulfonamide in 40 ml of dimethylformamide is added dropwise. The reaction mixture is stirred for 30 minutes at 35°-40° C. and then taken up in a mixture of 275 ml of ethyl acetate, 275 ml of icewater and 137.5 ml of 2N hydrochloric acid. The organic phase is separated and the aqueous phase is extracted with 3×100 ml of ethyl acetate. The combined organic phases are washed with 4×100 ml of water, dried, concentrated by evaporation and the residue is triturated with ether/hexane (2:1). The crystals so obtained are isolated and dried, affording 22.25 g of 2-cyclopropylmethoxypyridin-3-ylsulfonamide with a melting point of 121°-122° C.

Workup

  1. stirringThe reaction mixture is stirred for 30 minutes at 35°-40° C.
  2. customThe organic phase is separated
  3. extractionthe aqueous phase is extracted with 3×100 ml of ethyl acetate
  4. washThe combined organic phases are washed with 4×100 ml of water
  5. customdried
  6. concentrationconcentrated by evaporation
  7. customthe residue is triturated with ether/hexane (2:1)
  8. customThe crystals so obtained
  9. customare isolated
  10. customdried

Sources & evidence

ORD record
ord-b2df9c2830d84628a8110503f464f09c
Source dataset
uspto-grants-1988_10
Patent number
US04778513

Reaction notes

Loading…