Reacción #497538

Ecuación de reacción

1-(3-bromo-propoxy)-4-fluoro-benzene

1-(4-bromo-benzyl)-6-methyl-1,3-dihydro-benzoimidazol-2-ylideneamine

1-(3-bromo-propoxy)-4-fluoro-benzene

→

3-(4-bromo-benzyl)-1-[3-(4-fluoro-phenoxy)-propyl]-5-methyl-1,3-dihydrobenzoimidazol-2-ylideneamine, hydrobromide salt

Rendimiento 33.1%

Disolventes

2-butanone

2-butanone

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was heated
2. 2
   Temperaturato reflux where it
3. 3
   Temperaturawas maintained for 48 h
4. 4
   TemperaturaThe reaction was then heated
5. 5
   Temperaturato reflux for a further 15 h
6. 6
   TemperaturaIt was then cooled to rt
7. 7
   Filtraciónfiltered
8. 8
   OtroThe collected solid was dried

Procedimiento

To a solution of 1-(4-bromo-benzyl)-6-methyl-1,3-dihydro-benzoimidazol-2-ylideneamine (0.14 g, 0.44 mmol) in 2-butanone (5 ml) at rt was added 1-(3-bromo-propoxy)-4-fluoro-benzene (0.15 g, 0.66 mmol). The reaction was stirred for 10 min and then additional 2-butanone (5 ml) was introduced. The mixture was heated to reflux where it was maintained for 48 h. After this time, the reaction was cooled to rt and additional 1-(3-bromo-propoxy)-4-fluoro-benzene (0.05, 0.22 mmol) was added. The reaction was then heated to reflux for a further 15 h. It was then cooled to rt and filtered. The collected solid was dried to provide 3-(4-bromo-benzyl)-1-[3-(4-fluoro-phenoxy)-propyl]-5-methyl-1,3-dihydrobenzoimidazol-2-ylideneamine, hydrobromide salt (0.04 g, 16%). HPLC-MS 468, 470 [M+1]+.

Fuente