Iodoethane → 2-Ethyl-4-hydroxy-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxylic acid methyl ester-1,1-dioxide

Participants

Reaction Steps

33 ml of 1 N sodium hydroxide were added dropwise over a period of 25 minutes to a suspension of 10.1 gm (0.033 mol) of 4-hydroxy-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxylic acid methyl ester-1,1-dioxide and 20 gm (0.12 mol) of ethyl iodide in 400 ml of aqueous 75% ethanol, whereby the starting material went completely into solution. The reaction mixture was then stirred at room temperature for 30hours. Thereafter, the crystals which had formed were collected by filtration and washed with a small quantity of ethanol, yielding 8.7 gm (79% of theory) of the desired compound, m.p. 179° C (from ethanol).

Provenance & Evidence