HCID 10316709, compound → HCID 9997023, compound

Participants

Reaction Steps

To a solution of 2.46 g (6.76 mmole) of 3 -n- butyl-5-(carbomethoxymethylthio)-4-(4-nitrobenzyl)-4H-1,2,4-triazole in 32 ml of tetrahydrofuran stirred in an ice bath was added gradually over 15 minutes a solution of 15.2 g (67.6 mmole) of stannous chloride dihydrate in 19 ml of concentrated HCl. The ice bath was removed, and the mixture was stirred at room temperature for 1.5 hours. It was then poured into a vigrously stirred mixture of 68 ml of 50% NaOH and 270 g. of ice. This was rapidly extracted with 3×300 ml of ether. The combined ether extracts were washed with 150 ml of H2O, then dried (MgSO4), filtered, and concentrated to give 566 mg (25%) of a white waxy solid, homogeneous by TLC in 97:3 CHCl3 -iPrOH; mass spectrum (FAB) m/e 335 (M+1)+. This material was used directly in the next reaction.

Provenance & Evidence