Reaktion #58697

Reaktionsgleichung

2-cyano-N-phenyl-thioacetamide

1,3-dimethyluracil

sodium methoxide

EtOH

→

title compound

Sodium 3-cyano-6-oxo-1-phenyl-1,6-dihydro-pyridine-2-thiolate

Lösungsmittel

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe resulting mixture was heated
2. 2
   Temperaturat reflux for 8 h
3. 3
   TemperaturThe reaction mixture was then cooled to +5°
4. 4
   Temperaturmaintained at this temperature for at least an hour when the product
5. 5
   Filtrationwas recovered by filtration
6. 6
   WaschenThe filter cake was washed with cold (+5°) absolute ethanol (450 mL)
7. 7
   Sonstigedried to constant weight under vacuum at 45°

Vorschrift

A solution of sodium methoxide in MeOH (30 wt %, 202.2 g) was added to absolute EtOH (360 mL) followed by 1,3-dimethyluracil (75 g) and 2-cyano-N-phenyl-thioacetamide (Adhikari et al, Australian J. Chem., 1999, 52, 63-67) (90 g). The resulting mixture was heated at reflux for 8 h and then allowed to cool to ambient temperature overnight. The reaction mixture was then cooled to +5° and maintained at this temperature for at least an hour when the product was recovered by filtration. The filter cake was washed with cold (+5°) absolute ethanol (450 mL) and then dried to constant weight under vacuum at 45° to give the title compound as a pale pink solid (130.0 g). The product thus obtained contains residual EtOH and MeOH, estimated at 12.2 wt % by 1H nmr, corresponding to a corrected yield of 114.1 g. δH (DMSO-d6) 7.32 (2H, m), 7.27-7.18 (1H, m), 7.16 (1H, d, J 9.1 Hz), 6.92 (2H, m), 5.63 (1H, d, J 9.1 Hz). LCMS(Conditions B) (ES+) RT 2.43 minutes, 229 (M+H)+.

Quelle