Potassium Carbonate → 3-(2-Chloroethoxy)-pyrid-2-ylsulfonamide

HRID 55547Notes

Reaction equation

HRID 55547 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][CH2:8][CH2:9]C1C=C(S([O-])(=O)=O)C=CC=1C.[OH:21][C:22]1[C:23]([S:28]([NH2:31])(=[O:30])=[O:29])=[N:24][CH:25]=[CH:26][CH:27]=1>CC(N(C)C)=O>[Cl:7][CH2:8][CH2:9][O:21][C:22]1[C:23]([S:28]([NH2:31])(=[O:30])=[O:29])=[N:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 199579383-Hydroxypyridine-2-sulfonamideHCID 22572093HCID 22572093, compound

Product 1

HCID 199579443-(2-Chloroethoxy)-pyrid-2-ylsulfonamideYield 61%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

First 17.9 g of potassium carbonate and then 28.14 g of 2-(2-chloroethyl)-toluene-4-sulfonate are added, with stirring, to a solution of 17.4 g of 3-hydroxy-pyrid-2-ylsulfonamide in 240 ml of dimethylacetamide. The reaction mixture is stirred for 1.5 hours at 80° C. and then cooled and filtered. The filtration residue is washed with acetonitrile. The filtrate and the washing liquid are adjusted to pH 5-6 with trifluoroacetic acid, filtered and concentrated using a rotary evaporator. For purification the residue is chromatographed on a silica gel column using ethyl acetate/n-hexane 4/1. Removal of the eluant by evaporation yields 14.42 g of the above sulfonamide in the form of colourless crystals which melt at 136°-138° C.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. washThe filtration residue is washed with acetonitrile
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customa rotary evaporator
  7. customFor purification the residue
  8. customis chromatographed on a silica gel column
  9. customRemoval of the eluant
  10. customby evaporation

Sources & evidence

ORD record
ord-51951e1ab7bc45e8856cb280caf4d2bf
Source dataset
uspto-grants-1997_04
Patent number
US05625071

Reaction notes

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