Thiophosgene → 3-(Isothiocyanatomethyl)furan

Beteiligte Stoffe

Reaktionsschritte

To a solution of 3-(aminomethyl)furan (0.565 g, 5.818 mmol) in 10 mL of CHCl3 at 0° C. was added 10 mL of a saturated NaHCO3 solution and thiophosgene (0.66 mL, 8.66 mmol). The reaction mixture was stirred vigorously for 45 min while maintaining the temperature at between 0°-5° C. The phases were then separated and the aqueous layer extracted with CHCl3 (10 mL). The combined organic solutions were dried (MgSO4), filtered, and the volatiles removed by blowing a gentle stream of nitrogen over the solution. Traces of residual solvent and thiophosgene were then evaporated off under high vacuum (20° C./0.05 mm Hg) to afford 0.659 g,(81 percent of theoretical) of 3-(isothiocyanatomethyl)furan as a dark orange liquid which was found to be pure by NMR and suitable for use in the Diels-Alder step: 1H NMR (300 MHz, CDCl3) d 7.45 (s, 1H), 7.42 (s, 1H), 6.42 (s, 1H), 4.54 (s, 2H); 13C NMR (75 MHz, CDCl3) d 144.0, 139.9, 132.7, 119.5, 109.4, 40.2 ; IR (neat) 2090, 1595 cm-1; MS m/e 139, 81 (base).

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