Reaction #6673

Reaction equation

phenothiazine

iodoethane

potassium hydroxide

→

10-Ethylphenothiazine

Solvents

toluene

Conditions

Workup

1. 1
   Temperaturewas refluxed for 24 hours
2. 2
   TemperatureAfter cooling
3. 3
   Filtrationthe reaction mixture was filtered
4. 4
   Otherthe solvent was evaporated
5. 5
   OtherThe product was crystallized from methanol

Procedure

A mixture of 10 g (0.05 mol) of phenothiazine, 11.7 g (0.075 mol) of iodoethane, 4.2 g (0.075 mol) of potassium hydroxide and 0.25 g of tetra-n-butylammonium hydrogen sulfate in 200 ml of dry toluene was refluxed for 24 hours. After cooling, the reaction mixture was filtered, and the solvent was evaporated. The product was crystallized from methanol. The yield of 10-ethylphenothiazine (C14H13NS, FW=227.33) was 90%.

Source