Iodoethane → N-Ethylphenothiazine

Participants

Reaction Steps

A mixture of 10 g (0.05 mol) of phenothiazine (from Fluka), 11.7 g (0.075 mol) of iodoethane (from Aldrich), 4.2 g (0.075 mol) of potassium hydroxide, and 0.25 g of tetra-n-butylammonium hydrogen sulfate (from Aldrich) in 200 ml of dry toluene was refluxed for 24 hrs. The cooled reaction mixture was filtered and the solvent was evaporated. The product was recrystallized from methanol. The yield of 10-ethylphenothiazine was 10.2 g (90%). The product had a melting point of 103–104° C. (recrystallized from methanol). A 1H NMR spectrum yielded the following results (100 MHz, CDCl3, δ, ppm): 1.40 (t, J=7.0 Hz, 3H, CH3); 3.90 (q, J=7.0 Hz, 2H, CH2); 6.78–7.32 (m, 8H, Ar).

Provenance & Evidence