Reacción #2170604

Ecuación de reacción

hydrogen sulphide

phosphorus pentasulphide

octahydroacridine-4-carboxamide

hydrogen sulphide

→

Octahydroacridine-4-thiocarboxamide

Disolventes

pyridine

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaheated
2. 2
   Temperaturaat reflux for 45 mins
3. 3
   OtroThe cooled reaction mixture
4. 4
   Otrowas evaporated
5. 5
   workup.ADDITIONthe residue treated with 10% sodium hydroxide until alkaline
6. 6
   ExtracciónThe aqueous solution was extracted with chloroform (3 × 50 ml.)
7. 7
   Lavadothe combined extracts washed with brine
8. 8
   Otrodried
9. 9
   Otroevaporated
10. 10
    Otrothe residual solid recrystallised from di-isopropyl ether giving the title compound as a pale yellow powder (0.3 g. 16%) m.p. 104-6° (solidifies and remelts at 148°)

Procedimiento

A solution of sym. octahydroacridine-4-carboxamide (1.8 gm.) in pyridine (17 ml.) was treated with hydrogen sulphide for 5 mins. The reaction mixture was treated with phosphorus pentasulphide (1.4 g.) and heated at reflux for 45 mins maintaining a slow stream of hydrogen sulphide throughout. The cooled reaction mixture was evaporated and the residue treated with 10% sodium hydroxide until alkaline. The aqueous solution was extracted with chloroform (3 × 50 ml.) and the combined extracts washed with brine, dried and evaporated and the residual solid recrystallised from di-isopropyl ether giving the title compound as a pale yellow powder (0.3 g. 16%) m.p. 104-6° (solidifies and remelts at 148°). (Found: C, 68.69; H, 7.54; N, 10.98%. C14H18N2S requires: C, 68.26; H, 7.36; N, 11.37%).

Fuente