Cyanogen Bromide → 2-(7-Methoxy-6-Methyl-1,2,3,4-Tetrahydronaphthyl)-2-Imidazolinecarbonitrile

Participants

Reaction Steps

In a 9.5 dram screw cap vial was placed 0.20 gram (0.0008 mole) of Compound 50 (prepared as set forth in Example 2), 0.11 gram (0.0008 mole) of N,N-diisopropylethylamine, and 25 mL of methylene chloride; followed by 2.4 mL (0.0008 mole) of a stock solution of 1 mL of cyanogen bromide in 30 mL of methylene chloride. The reaction mixture was then gently shaken during an 18 hour period using a mechanical shaker. After this time the reaction mixture was poured into ice water in a separatory funnel, and the mixture was extracted with three portions of methylene chloride. The combined extracts were dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residual oil. The residual oil was purified by column chromatography on Grade II alumina (basic-3% water) using methylene chloride as an eluant. The appropriate fractions of eluate were combined and concentrated under reduced pressure, yielding 0.19 gram of Compound 201. The NMR spectrum was consistent with the proposed structure.

Provenance & Evidence