Dimethyl Sulfoxide → HCID 21464407, compound

HRID 1940912Notes

Reaction equation

HRID 1940912 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH:9][S:10]([C:13]1[N:22]=[C:16]2[C:17](Cl)=[CH:18][CH:19]=[CH:20][N:15]2[N:14]=1)(=[O:12])=[O:11].[CH3:23][O-:24].[Na+].CS(C)=O.C[O-].[K+]>CO.ClCCl.C(O)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH:9][S:10]([C:13]1[N:22]=[C:16]2[C:17]([O:24][CH3:23])=[CH:18][CH:19]=[CH:20][N:15]2[N:14]=1)(=[O:12])=[O:11]

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 10942334Sodium Methoxide2×HCID 21464436HCID 21464436, compoundHCID 23664618Potassium methoxide

Product 1

HCID 21464407HCID 21464407, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

N-(2,6-Difluorophenyl)-8-chloro[1,2,4]triazolo[1,5-a]pyridine-2-sulfonamide (0.8 g, 0.0023 mol) and 25 percent sodium methoxide in methanol (1.6 mL, 0.37 g, 0.007 mol) were combined with 20 mL of dimethyl sulfoxide and the resulting solution was stirred at ambient temperature overnight. Another 1.6 mL of 25 percent sodium methoxide in methanol was added and the reaction mixture was stirred another 3 days. The mixture was then acidified with acetic acid and diluted with dichloromethane. The resulting solution was washed well with water and concentrated by evaporation under reduced pressure. The residue, which appeared to contain considerable starting material, was dissolved in 20 mL of dimethyl sulfoxide and potassium methoxide (0.4 g, 0.0057 mol) was added with stirring at ambient temperature. After about 3 hours the mixture was acidified with acetic acid and diluted with dichloromethane. The resulting solution was washed well with water and concentrated by evaporation under reduced pressure. The residue was mixed with hexane and the solids present were collected by filtration, washed with ether and with dichloromethane and dried to obtain 0.30 g (38 percent of theory) of the title compound as a white powder melting at 254°-255° C.

Workup

  1. stirringthe reaction mixture was stirred another 3 days
  2. washThe resulting solution was washed well with water
  3. concentrationconcentrated by evaporation under reduced pressure
  4. dissolutionwas dissolved in 20 mL of dimethyl sulfoxide
  5. stirringwith stirring at ambient temperature
  6. washThe resulting solution was washed well with water
  7. concentrationconcentrated by evaporation under reduced pressure
  8. additionThe residue was mixed with hexane
  9. filtrationthe solids present were collected by filtration
  10. washwashed with ether and with dichloromethane
  11. customdried

Sources & evidence

ORD record
ord-58dff160d2154d8194627558964ade26
Source dataset
uspto-grants-1997_12
Patent number
US05700940

Reaction notes

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