Dimethyl Sulfoxide → HCID 10863354, compound

Participants

Reaction Steps

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.

Provenance & Evidence