Thiophosgene → 3-(Isothiocyanatomethyl)furan

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).

1. temperaturewhile maintaining the temperature at between 0°-5° C
2. customThe phases were then separated
3. extractionthe aqueous layer extracted with CHCl3 (10 mL)
4. dry with materialThe combined organic solutions were dried (MgSO4)
5. filtrationfiltered
6. customthe volatiles removed
7. customTraces of residual solvent and thiophosgene were then evaporated off under high vacuum (20° C./0.05 mm Hg)

ORD-Eintrag

ord-01055551705c4853a92a6f26e02fadb0

Quelldatensatz

uspto-grants-1996_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05505931