Ethyl Acetate → HCID 54269281, compound

Participants

Reaction Steps

The diamine obtained in Step C (1.08 g) was dissolved in glacial acetic acid (20 cm3) and water (2 cm3) and cooled to below 5° C. in an ice/salt bath. A solution of sodium nitrite (0.41 g, 5.9 mmol) in water (5 cm3) was added dropwise, at such a rate that the internal temperature was maintained below 5° C., and when the addition was complete the reaction mixture was stirred for 4 hours, during which it was allowed to warm to room temperature. The mixture was poured into ethyl acetate (100 cm3) and washed successively with water (2×100 cm3) and saturated aqueous sodium bicarbonate solution (100 cm3). The organic phase was dried (MgSO4), filtered and the filtrate evaporated under reduced pressure. The residue was further purified by flash column chromatography on silica gel, eluting with diethyl ether, to give compound 9, DL 2-[6-(4-chloro-1-methyl-5-trifluoromethyl-1H-pyrazol-3-yloxy) benzotriazol-1-yl]-propan-1-ol (0.90 g) as an off white solid m.p. 153°-154° C.

Provenance & Evidence