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

HRID 1707238Notes

Reaction equation

HRID 1707238 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-fluoropropythio)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-d24595bd7fc04b369ced0cfade629980
Source dataset
uspto-grants-1994_10
Patent number
US05352654

Reaction notes

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