Reaction #40265

Reaction equation

4-[bis(2-hydroxyethyl)-amino]benzaldehyde

1,1′-{disulfanediylbis[ethane-2,1-diylimino(2-oxoethane-2,1-diyl)]}bis(2,3-dimethyl-1H-benzimidazol-3-ium) chloride

→

orange solid

Yield 163.3%

1,1′-{disulfanediylbis[ethane-2,1-diylimino(2-oxoethane-2,1-diyl)]}bis{2-[2-{4-[bis(2-hydroxyethyl)amino]phenyl}ethenyl]-3-methyl-1H-benzimidazol-3-ium}chloride

Yield 163.3%

Solvents

ethanol

piperidine

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was heated
2. 2
   Temperatureto reflux for 7 h
3. 3
   TemperatureAfter cooling
4. 4
   Filtrationthe resulting orange solids were collected by filtration
5. 5
   Washwashed with dichloromethane and methanol

Procedure

To a stirring solution of 4-[bis(2-hydroxyethyl)-amino]benzaldehyde (1.7 g, 8.1 mmol) and 1,1′-{disulfanediylbis[ethane-2,1-diylimino(2-oxoethane-2,1-diyl)]}bis(2,3-dimethyl-1H-benzimidazol-3-ium) chloride (1.2 g, 2 mmol) in 35 ml of ethanol, 0.5 ml of piperidine was added as a catalyst. The reaction mixture was heated to reflux for 7 h. After cooling, the resulting orange solids were collected by filtration and then washed with dichloromethane and methanol. The drying afforded 1.6 g of a orange solid. Analyses were in accordance with the expected structure.

Source