Dimethyl Sulfoxide → HCID 18985858, compound

HRID 2396683Notes

Reaction equation

HRID 2396683 reaction equation
Cl[S:2]([C:5]1[N:13]=[C:12]2[N:7]([C:8]([O:18][CH3:19])=[N:9][C:10]3[N:17]=[CH:16][CH:15]=[CH:14][C:11]=32)[N:6]=1)(=[O:4])=[O:3].[Cl:20][C:21]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:22]=1[NH2:23].N1C=CC=CC=1.CS(C)=O>C(#N)C>[Cl:20][C:21]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:22]=1[NH:23][S:2]([C:5]1[N:13]=[C:12]2[N:7]([C:8]([O:18][CH3:19])=[N:9][C:10]3[N:17]=[CH:16][CH:15]=[CH:14][C:11]=32)[N:6]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 1049PyridineHCID 118462,6-DichloroanilineHCID 18985855HCID 18985855, compound

Product 1

HCID 18985858HCID 18985858, compoundYield 8.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2.0 g (6.7 mmol) of 2-chlorosulfonyl-5-methoxypyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine, 2.2 g (13.3 mmol) of 2,6-dichloroaniline, 0.50 g (67 mmol) of pyridine, and 30 mL of dry acetonitrile was prepared and to this was added with stirring at ambient temperature 95 microliters (1.3mmol) of dimethyl sulfoxide. The mixture was allowed to react overnight and was then concentrated by evaporation under reduced pressure. The residue was diluted with dichloromethane and water and the resulting mixture was filtered to remove the insoluble solids. The organic phase was recovered and the dichloromethane was removed by evaporation under reduced pressure. The residue was diluted with hexane, recovered by filtration, and redissolved in dichloromethane. The resulting solution was filtered through silica gel and concentrated by evaporation under reduced pressure. The residue was diluted with hexane, recovered by filtration, and dried to obtain 0.25 g of the title compound as a light tan powder melting at 290°-293° C. with decomposition. The proton NMR spectrum of this was compatible with the assigned structure.

Workup

  1. customwas prepared
  2. additionto this was added
  3. customto react overnight
  4. concentrationwas then concentrated by evaporation under reduced pressure
  5. additionThe residue was diluted with dichloromethane and water
  6. filtrationthe resulting mixture was filtered
  7. customto remove the insoluble solids
  8. customThe organic phase was recovered
  9. customthe dichloromethane was removed by evaporation under reduced pressure
  10. additionThe residue was diluted with hexane
  11. filtrationrecovered by filtration
  12. dissolutionredissolved in dichloromethane
  13. filtrationThe resulting solution was filtered through silica gel
  14. concentrationconcentrated by evaporation under reduced pressure
  15. additionThe residue was diluted with hexane
  16. filtrationrecovered by filtration
  17. customdried

Sources & evidence

ORD record
ord-50920b213fc743c58e35e6a9e76e3223
Source dataset
uspto-grants-1996_02
Patent number
US05494887

Reaction notes

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