p-Toluenesulfonic acid monohydrate → HCID 10198961, compound

Participants

Reaction Steps

To a solution of the diamine of Step A (3.8 g) in dioxane (100 mL) under nitrogen was added 1,1′-thiocarbonyl-di-1,2,4-triazole (3.38 g). After 45 minutes additional thiocarbonyl reagent (0.5 g) was added, followed after 30 minutes by para-toluenesulfonic acid monohydrate (6.88 g). The reaction mixture was heated at reflux for 4 hours at which point additional para-toluenesulfonic acid monohydrate (2.0 g) was added. After refluxing for 18 hours, another portion of para-toluenesulfonic acid monohydrate (1.5 g) was added. The reaction mixture was refluxed for an additional 24 hours, cooled and concentrated in vacuo to give a brown oil which crystallized on standing. The crude material was dissolved in dichloromethane and absorbed onto a column of Merck-60 flash silica gel. Elution with 20% ethyl acetate in hexane provided a light pink solid which was triturated with diethyl ether to give the title compound (2.9 g, 63.9%) as a white solid, m.p. 143-145° C.

Provenance & Evidence