Toluene → HCID 9815601, compound

Participants

Reaction Steps

Triethylamine (0.017 mL, 0.12 mmol, 0.1 eq), 2-(2-ethylsulfinyl) benzoyl pyrrole (0.3 g, 1.2 mmol), and toluene (15 mL) are combined and refluxed with stirring for 24 hours. After removal of volatiles in vacuo, a light brown oil is obtained which solidifies to a dark gold solid. Chromatography of the crude solid with a 1:1 ratio of CHCl3 to hexanes yields a product mix comprising 24 mg (0.12 mmol, 15 percent) of pyrrolo(2,1-b)-(1,3)benzothiazin-9-one, 114 mg (0.57 mmol, 69 percent) of pyrrolo(2,1-b)-(1,2)benzothiazin-10-one and 115 mg of light brown solid which proves by NMR to be a mixture of recovered starting material and 1H, 9H-(1)benzothiopyrano(3,2-b)pyrrol-9-one. By integration, the following approximate amounts for the above mixture are calculated: 93 mg (0.38 mmol) and 22 mg (0.11 mmol, 13 percent), respectively.

Provenance & Evidence