Dimethyl Sulfoxide → HCID 14155248, compound

HRID 1645968Notes

Reaction equation

HRID 1645968 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:23]=[C:17]2[N:18]=[C:19]([CH3:22])[CH:20]=[CH:21][N:16]2[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:23]=[C:17]2[N:18]=[C:19]([CH3:22])[CH:20]=[CH:21][N:16]2[N:15]=1)(=[O:12])=[O:13]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 1049PyridineHCID 118462,6-DichloroanilineHCID 141551085-Methyl[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonyl chloride

Product 1

HCID 14155248HCID 14155248, compoundYield 52.6%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8058HexaneSolvent

Procedure

2,6-Dichloroaniline (2.78 g, 17.2 mmol), 2-chlorosulfonyl-5-methyl-1,2,4-triazolo[1,5-a]pyrimidine (2.0 g, 8.6 mmol), and 30 mL of dry acetonitrile were placed in a 100 mL flask equipped with a gas inlet adapter and a magnetic stirring bar. Pyridine (1.39 mL, 17.2 mmol) and dimethyl sulfoxide (0.15 mL, 2.2 mmol) were added with stirring under nitrogen and the mixture was allowed to react for 1.0 hr. The volatiles were then removed by evaporation under reduced pressure and the residue was dissolved in 200 mL of methylene chloride. The solution obtained was extracted 2 times with 100 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 white solid. This solid was stirred with 200 mL of hexane and filtered to give 1.62 g (52 percent yield) of the title compound as a white solid melting at 126°-129° C. (d).

Workup

  1. customequipped with a gas inlet adapter and a magnetic stirring bar
  2. customto react for 1.0 hr
  3. customThe volatiles were then removed by evaporation under reduced pressure
  4. dissolutionthe residue was dissolved in 200 mL of methylene chloride
  5. customThe solution obtained
  6. extractionwas extracted 2 times with 100 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 white solid
  11. filtrationfiltered

Sources & evidence

ORD record
ord-8e08426c06e74cd285ce77ab75240c74
Source dataset
uspto-grants-1993_01
Patent number
US05177206

Reaction notes

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