Reaction #985274

Reaction equation

phenothiazine

1,6-dibromohexane

potassium hydroxide

→

1,6-Di(10H-10-phenothiazinyl)hexane

Solvents

toluene

Conditions

Workup

1. 1
   Temperaturerefluxed for 48 hours
2. 2
   Filtrationfiltered
3. 3
   Washwashed thoroughly with water
4. 4
   DryingThe organic phase was dried over anhydrous sodium sulfate
5. 5
   Otherthe solvent was removed by evaporation
6. 6
   OtherThe crude product was purified by column chromatography
7. 7
   workup.ADDITIONa mixture of ethyl acetate and hexane in a volume ratio of 1:6 as eluent

Procedure

A mixture of phenothiazine (0.15 mol), 0.1 mol of 1,6-dibromohexane, 0.15 mol of potassium hydroxide and 1% w/w of tetra-n-butyl ammonium hydrogen sulfate in 300 ml of dry toluene was stirred and refluxed for 48 hours. The reaction mixture was cooled to room temperature, filtered, and washed thoroughly with water. The organic phase was dried over anhydrous sodium sulfate, and the solvent was removed by evaporation. The crude product was purified by column chromatography using a mixture of ethyl acetate and hexane in a volume ratio of 1:6 as eluent. The yield of 1,6-di(10H-10-phenothiazinyl)hexane was 85%. The 1H-NMR spectrum of the product in CDCl3 was characterized by the following chemical shifts (δ, ppm): 1.35-1.50(m, 4H), 1.55-1.90(m, 4H), 3.82(t, 4H), and 6.73-7.19(m, 16H).

Source