Hydrochloric Acid → 3-(3-Fluoropropylthio)pyridin-2-ylsulfonamide

HRID 1655069Notes

Reaction equation

HRID 1655069 reaction equation
[SH:1][C:2]1[C:3]([S:8]([NH2:11])(=[O:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[F:18][CH2:19][CH2:20][CH2:21]Br.Cl>CN(C)C=O>[F:18][CH2:19][CH2:20][CH2:21][S:1][C:2]1[C:3]([S:8]([NH2:11])(=[O:9])=[O:10])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 67699Propane, 1-bromo-3-fluoro-HCID 1274273-Mercaptopyridine-2-sulfonamide

Product 1

HCID 200775483-(3-Fluoropropylthio)pyridin-2-ylsulfonamideYield 32%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture consisting of 0.285 g of 3-mercaptopyridin-2-ylsulfonamide, 0.455 g of potassium carbonate, 5 ml of dry dimethylformamide and 0.23 g of 3-fluoro-1-bromopropane is stirred for 90 minutes at a temperature of +25° C. in a nitrogen atmosphere. The reaction mixture is subsequently added to an ice/water mixture. After a pH of 2 has been established with 2.8 ml of 2N HCl, the reaction mixture is extracted twice with ethyl acetate. The combined organic phases are washed three times with water and subsequently dried over sodium sulfate. Concentration and subsequent chromatographic purification of the residue over silica gel with ethyl acetate/n-hexane (1:1) give 0.12 g of 3-(3-fluoropropylthio)pyridin-2-ylsulfonamide of a melting point of +85° to +86° C.

Workup

  1. extractionthe reaction mixture is extracted twice with ethyl acetate
  2. washThe combined organic phases are washed three times with water
  3. dry with materialsubsequently dried over sodium sulfate
  4. concentrationConcentration and subsequent chromatographic purification of the residue over silica gel with ethyl acetate/n-hexane (1:1)

Sources & evidence

ORD record
ord-fe3c6a60bf9b4dde916c1d58aeaba295
Source dataset
uspto-grants-1995_04
Patent number
US05410063

Reaction notes

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