Reaction #2195468

Reaction equation

N-(2-bromoethyl)-4-[(4-chloro-5-nitro-1,3-thiazol-2-yl)diazenyl]-N-ethylaniline

1-methyl-1H-imidazole

→

1-{2-[{4-[(4-chloro-5-nitro-1,3-thiazol-2-yl)diazenyl]phenyl}(ethyl)amino]ethyl}-3-methyl-1H-imidazol-3-ium bromide

Yield 30.0%

Solvents

acetonitrile

Conditions

Workup

1. 1
   Temperatureunder reflux for 3 days
2. 2
   FiltrationThe resulted precipitate is filtered off
3. 3
   Washwashed with acetonitrile
4. 4
   Otherdried in vacuum at 40° C

Procedure

1.20 g N-(2-bromoethyl)-4-[(4-chloro-5-nitro-1,3-thiazol-2-yl)diazenyl]-N-ethylaniline is dissolved in 20 ml acetonitrile followed by subsequent addition of 5.99 g 1-methyl-1H-imidazole. The reaction mixture is stirred under reflux for 3 days and allowed to cool to room temperature. The resulted precipitate is filtered off, washed with acetonitrile, and dried in vacuum at 40° C. 0.43 g 1-{2-[{4-[(4-chloro-5-nitro-1,3-thiazol-2-yl)diazenyl]phenyl}(ethyl)amino]ethyl}-3-methyl-1H-imidazol-3-ium bromide is obtained as a bordeaux red powder.

Source