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314 J. Am. Chem. SOC.1990, 112, 374-381 Preparation of Labled Diazirine [15N#24. 3-(Trifluoromethyl)-
 

Summary: 314 J. Am. Chem. SOC.1990, 112, 374-381
Preparation of Labled Diazirine [15N#24. 3-(Trifluoromethyl)-
benzonitrile (2.983g, 0.0172mol)was dissolved in 17 mL of anhydrous
methanol, and 1.0 mL of 1.88 M NaOMe in methanol (0.001 88 mol)
was added under nitrogen. The reaction mixture was stoppered and
allowed to stir for 48 h at room temperature. ISN-Labeledammonium
chloride (0.9688g. 0.0183 mol of 99.1%15Nenriched, Isotech, Inc.) was
added and the suspension stirred for 35 h at room temperature. The
mixture was filtered, and the unreacted ammonium chloride in the filter
was washed with a small amount of anhydrous methanol. The combined
filtrates were concentrated with a rotary evaporator, and the crystals were
slurried with ether. The ether was then decanted. This procedure was
carried out a total of five times in order to remove unreacted 3-(tri-
fluoromethy1)benzonitrile. The yield of 'SN-tabeled 3-(trifluoro-
methy1)benzamidine hydrochloride was 3.0448 g (79%).
A NaOBr solution was prepared from 6.28 g of NaOH in 80 mL of
water by the addition of 6.60 g of bromine. When all the bromine had
reacted, 4.28 g of NaBr was added and the flask swirled to dissolve the
NaBr. This solution was used immediately in the oxidation of the 15N-
labeled 3-(trifluoromethyl)ben~m~dinehydrochloride. The salt prepared

  

Source: Apeloig, Yitzhak - Department of Chemistry, Technion, Israel Institute of Technology

 

Collections: Chemistry