Iodine → HCID 86597542, compound

To a solution of 2-(2-propenyl)-5-trifluoromethylbenzenesulfonamide (780 mg, 2.94 mmol) in nitrogen-degassed dichloromethane (30 mL) containing potassium carbonate (1.62 g, 11.8 mmol) was added iodine (1.49 g, 5.88 mmol). After stirring for 2 h, the reaction was quenched with 10% aqueous sodium thiosulfate (ca. 14 mL). The dichloromethane was removed in vacuo and the residue was diluted with methanol (10 mL) and 0.25 N potassium carbonate in 70% aqueous methanol. Additional methanol was added to produce a nearly homogeneous solution. After 10 min, the reaction was concentrated in vacuo to remove most of the methanol. The residue was partitioned between dichloromethane (30 mL) and water (10 mL). The aqueous layer was extracted with dichloromethane (5 mL) and the combined organic layers were dried (magnesium sulfate) and concentrated in vacuo to provide 8,8a-dihydro-5-(trifluoromethyl)-1H-azirino[1,2-b][1,2]benzothiazine 3,3-dioxide as a white solid (685 mg (92%): LCMS (net. ion spectrum) m/z 262.

1. customthe reaction was quenched with 10% aqueous sodium thiosulfate (ca. 14 mL)
2. customThe dichloromethane was removed in vacuo
3. additionthe residue was diluted with methanol (10 mL) and 0.25 N potassium carbonate in 70% aqueous methanol
4. additionAdditional methanol was added
5. customto produce a nearly homogeneous solution
6. waitAfter 10 min
7. concentrationthe reaction was concentrated in vacuo
8. customto remove most of the methanol
9. customThe residue was partitioned between dichloromethane (30 mL) and water (10 mL)
10. extractionThe aqueous layer was extracted with dichloromethane (5 mL)
11. dry with materialthe combined organic layers were dried (magnesium sulfate)
12. concentrationconcentrated in vacuo

ORD record

ord-e288b1176b70488caa6401c26119c233

Source dataset

uspto-grants-2007_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07244843B2