Methanesulfonyl chloride → HCID 10665443, compound

Participants

Reaction Steps

A solution of 4-amino-7-chloro-3-phenyl-2(1H)-quinolone (0.55 g, 2 mmol) (Example 2) and potassium (bistrimethylsilyl) amide (4 ml, 0.5M solution in toluene) in 50 ml tetrahydrofuran were stirred for 10 mins prior to the addition of tert-butyldimethylsilyl trifluoromethanesulfonate (6.1 ml). After a further 10 mins a further portion of potassium(bistrimethylsilyl)amide (6.1 ml) was added followed after 10 mins by methanesulfonyl chloride (0.48 ml). The solvent was removed in vacuo after one hour and the residue was suspended in 5N HCl (30 ml), and treated with ultrasound for 5 mins before being filtered. The solid was suspended in 1N NaOH and re-exposed to ultrasound then filtered to give the title compound (0.077 g); mp 222°-224° C. (DMF-water-diethyl ether); δ (360 MHz, DMSO-d6) 2.17 (3H, s, CH3), 7.34-7.67 (8H, m, aromatics), 9.60 (1H, br s, NHSO2), 12.16 (1H, br s, NHCO); m/z (EI) 348 (M+).

Provenance & Evidence