Dimethyl Sulfoxide → HCID 10863354, compound

HRID 1645963Notes

Reaction equation

HRID 1645963 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:3]=1[NH2:4].Cl[S:11]([C:14]1[N:22]=[C:21]2[N:16]([C:17]([O:24][CH3:25])=[N:18][CH:19]=[C:20]2[Br:23])[N:15]=1)(=[O:13])=[O:12].N1C=CC=CC=1.CS(C)=O>CCCCCC.C(#N)C>[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:3]=1[NH:4][S:11]([C:14]1[N:22]=[C:21]2[N:16]([C:17]([O:24][CH3:25])=[N:18][CH:19]=[C:20]2[Br:23])[N:15]=1)(=[O:12])=[O:13]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 1049PyridineHCID 118462,6-DichloroanilineHCID 11056528HCID 11056528, compound

Product 1

HCID 10863354HCID 10863354, compoundYield 52.8%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8058HexaneSolvent

Procedure

2,6-Dichloroaniline (1.76 grams (g), 10.9 mmol), 2-chlorosulfonyl-8-bromo-5-methoxy-1,2,4-triazolo[1,5-c]pyrimidine (1.5 g, 4.6 mmol), and 30 milliliters (mL) of dry acetonitrile were placed in a 100 mL flask equipped with a gas inlet adapter and a magnetic stirring bar. Pyridine (0.74 mL, 9.2 mmol) and dimethyl sulfoxide (0.08 mL, 1.2 mmol) were added with stirring under nitrogen and the mixture was allowed to react for 1.25 hours (hr). The volatiles were then removed by evaporation under reduced pressure and the residue was dissolved in 100 mL of methylene chloride. The solution obtained was extracted 3 times with 75 mL of 1N HCl and once with 100 mL of water, dried over MgSO4, filtered, and concentrated by evaporation under reduced pressure to obtain a yellow solid. This solid was diluted with 100 mL of hexane and, after standing for 1 hr, the hexane was removed by filtration and the solids washed with more hexane and dried to obtain 1.1 g (52 percent yield) of the title compound as a yellow solid melting at 192°-196° C.

Workup

  1. customequipped with a gas inlet adapter and a magnetic stirring bar
  2. customto react for 1.25 hours (hr)
  3. customThe volatiles were then removed by evaporation under reduced pressure
  4. dissolutionthe residue was dissolved in 100 mL of methylene chloride
  5. customThe solution obtained
  6. extractionwas extracted 3 times with 75 mL of 1N HCl
  7. dry with materialonce with 100 mL of water, dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated by evaporation under reduced pressure
  10. customto obtain a yellow solid
  11. customthe hexane was removed by filtration
  12. washthe solids washed with more hexane
  13. customdried

Sources & evidence

ORD record
ord-ee99657bae11417d96e58f0c948bb5db
Source dataset
uspto-grants-1993_01
Patent number
US05177206

Reaction notes

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