Sodium Iodide → HCID 67692893, compound

Participants

Reaction Steps

Under N2, 18-crown 6 (7.92 g, 0.03 mol) in CH2Cl2 (50 ml) and NaI (5 g, 0.033 mol) was stirred at room temperature. After 5 minutes, the reaction was cooled to 0°-4° C. and an ether solution of trans-5,6-dihydro-4-ethylamino-6-(2-methoxyethoxy) methyl-4H-thieno[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide (2.1g, 0.005 mol) was added. After addition, the reaction was stirred at room temperature for 0.5 hours and then cooled to -78° C. and BBr3 in CH2Cl2 (1M, 25 ml, 0.025 mol) was added. After the addition, the reaction was allowed to warm to 0° C. over 3 hours. The mixture was then concentrated to dryness and the residue was treated with 6N HCl (40 ml). After heating for 5 minutes in a steam bath, the reaction was cooled and neutralized to pH 8.5 with NaHCO3. The resulting mixture was extracted with EtOAc(3×) and the organic extracts were dried, filtered and concentrated to dryness. The residue was chromatographed on a Still silica gel column and the product eluted with 25-50% methanol-chloroform with 2.5 to 5.0% aqueous NH3 to yield crude product. The material was crystallized as the HCl salt from EtOH to yield 280 mg (13%) of the title compound; m.p. 157°-9° C.

Provenance & Evidence