Sulfuric Acid → HCID 53986262, compound

Participants

Reaction Steps

A stirred solution of 3.5 grams (0.014 mole) of 2-(2-propen-1-ylamino)-4-ethoxycarbonylamino-5-fluoroaniline in 100 mL of aqueous 1% sulfuric acid was cooled to about -5° C., and a solution of 1.9 grams (0.028 mole) of sodium nitrite dissolved in a minimum of water was added dropwise, while the reaction mixture temperature was held at about 0°-10° C. Upon completion of the addition, the reaction mixture was stirred for one hour and then poured into water. The mixture was made basic to a pH of 8 with potassium carbonate. The mixture was then extracted thoroughly with ethyl acetate. The combined extracts were washed with an aqueous solution saturated with sodium chloride, and then dried with magnesium sulfate. The mixture was filtered, and the filtrate was subjected to column chromatography on silica gel. Elution was accomplished with 1:3 ethyl acetate in hexane. The product-containing fractions were combined and concentrated under reduced pressure, yielding 0.8 gram of 1-(2-propen-1-yl)-5-fluoro-6-ethoxycarbonylaminobenzotriazole. The NMR spectrum was consistent with the proposed structure.

Provenance & Evidence