Dimethyl Sulfoxide → HCID 10863354, compound

HRID 1645966Notes

Reaction equation

HRID 1645966 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 26.3%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

2,6-Dichloroaniline (1.0 g, 6.2 mmol), 2-chlorosulfonyl-8-bromo-5-methoxy-1,2,4-triazolo[1,5-c]-pyrimidine (1.0 g, 3.1 mmol), and 20 mL of dry acetonitrile were placed in a 100 mL flask equipped with a gas inlet adapter and a magnetic stirring bar. The solution was cooled to 0° C. Pyridine (0.50 mL, 6.2 mmol) and dimethyl sulfoxide (0.06 mL, 0.8 mmol) were added with stirring under nitrogen and the mixture was allowed to react for 1 hr at 0° C. The volatiles were then removed by evaporation under reduced pressure and the residue was dissolved in 150 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 yellow solid. This solid was stirred with 200 mL of hexane and filtered to give 0.37 g (26 percent yield) of the title compound as a yellow solid melting at 196°-198° C. (d).

Workup

  1. customequipped with a gas inlet adapter and a magnetic stirring bar
  2. customto react for 1 hr at 0° C
  3. customThe volatiles were then removed by evaporation under reduced pressure
  4. dissolutionthe residue was dissolved in 150 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 yellow solid
  11. filtrationfiltered

Sources & evidence

ORD record
ord-30d811df9c5c4e22914811a08946ce26
Source dataset
uspto-grants-1993_01
Patent number
US05177206

Reaction notes

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