Methyl Ethyl Ketone → HCID 178477401, compound

Participants

Reaction Steps

A mixture of 2-(bromomethyl) saccharin (3 g, 10.8 mmol) and the sodium salt of 5-mercapto-1-methyl-1H-tetrazole (1.49 g, 10.8 mmol) was heated under reflux in methyl ethyl ketone (75 ml) for 2 hours. The reaction mixture was cooled, poured into dilute sodium bicarbonate/ice solution and extracted with MDC (2x's). The combined organic extracts were dried (Na2SO4) and freed of solvent under vacuum. The crude product was chromatographed (silica gel-95:5 CH2Cl2 :ether), and the resultant oil was crystallized from hot isopropanol to afford 2.7 g (80%) of 2-(1-methyl-1H-tetrazol-5-ylthiomethyl)saccharin as a white solid, mp 106°-110° C. 1H nmr (90 MHz, CDCl3):5.55 (2H, s). FDMS: m/e 311 (M+).

Provenance & Evidence