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-(ethyl-sulfonyl)-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 (1.0M 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 1N HCl, and poured into ethyl acetate (100 mL). The solution Was washed once with 1N HCl (100 mL). The 100 mL of 1N HCl wash was extracted With ethyl acetate (100 mL). The ethyl acetate solutions were combined and washed With 1N 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°14 202° C.

Provenance & Evidence