Dimethyl Sulfide → Penoxsulam

Participants

Reaction Conditions

Reaction Steps

A solution of methyl sulfide (0.34 g, 0.0055 mol) in acetonitrile (40 mL) was cooled to −25° C. To the cold solution was added a cold, freshly prepared 17 wt % solution of chlorine in acetonitrile (2.4 g, 0.0057 mol) over several minutes. While still cold, 1.1 g of 2-amino-5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidine (1.1 g, 0.0056 mol) and 3-picoline (0.95 g, 0.010 mol) were added. The mixture was allowed to warm to 8° C. 3-Picoline (48 g, 0.52 mol), 2-amino-5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidine (18.4 g, 0.094 mol), and 2-(2,2-difluoroethoxy)-6-(trifluoromethyl)benzenesulfonyl chloride (32.5 g, 0.10 mol) were added in order to the reactor. The mixture was stirred and heated at ˜40° C. for 24 hours, then at room temperature for 48 hours. The reaction slurry was converted into a solution by the addition of acetonitrile (600 mL) and water (100 mL). The solution was assayed for product by HPLC and determined to contain 42 g (86% yield, in situ, from sulfonyl chloride).

Provenance & Evidence