Ethanol → HCID 9803983, compound

Participants

Reaction Steps

To a stirred suspension of 8-chloro-2-methoxydibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-[3-(ethylsulfonyl)-1-oxopropyl]hydrazide (1.00 g), prepared in the manner described above in Example 3, in methylene chloride (5 mL) at approximately 5° C. (ice water bath) under nitrogen was added dropwise boron tribromide (1.0 M in 6.7 mL of methylene chloride). The ice bath was removed and the reaction stirred at room temperature for 3 hours. The reaction was carefully quenched by the addition of 1 N HCl, and poured into ethyl acetate (100 mL). The solution was washed once with 1 N HCl (100 mL). The 100 mL of 1 N HCl wash was extracted with ethyl acetate (100 mL). The ethyl acetate solutions were combined and washed with 1 N HCl, Water and brine. Evaporation of the solution in vacuo resulted in a semi-solid residue. This was treated With 10 mL of ethanol (3A) and heated on a steam bath for several minutes to break up the solid. Upon cooling, the solidified product Was collected by filtration. Recrystallization from ethanol (3A) yielded 0.44 g (45%) pure product as a white solid. Melting Point: 200°-202° C.

Provenance & Evidence