p-nitrophenol sodium salt → 2-[(4-Nitrophenoxy)methyl]-1H-1lambda~6~,2-benzothiazole-1,1,3(2H)-trione

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(chloromethyl) saccharin (3 g, 12.9 mmol) and sodium p-nitrophenoxide (2.55 g, 12.9 mmol) in THF (50 ml) was heated overnight at 50° C. and then refluxed for 45 minutes. The reaction mixture was cooled, poured into a dilute sodium bicarbonate/ice solution and extracted twice with ethyl acetate. The combined organic extracts were washed with sodium bicarbonate solution and water, dried (Na2SO4), and taken to dryness in vacuo. Chromatography (silica gel; MDC) afforded an oil that was crystallized from hot cyclohexane/ether. The resultant solid was recrystallized from ethanol to afford 0.92 g of 2-(4-nitrophenoxymethyl)-saccharin as white shiny platelets, mp 162°-164° C. 1H nmr (90 MHz, CDCl3, DMSO-d6):5.95 (2H, s). FDMS m/e 334 (M+).

Provenance & Evidence