Reacción #1801453

Ecuación de reacción

sodium bicarbonate

4,5-Dichloro-benzene-1,2-diamine

2,3,3,3-tetrafluoro-propionic acid

HCl

→

title compound

5,6-Dichloro-2-(1,2,2,2-tetrafluoro-ethyl)-1H-benzoimidazole

Disolventes

water

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled to room temperature
2. 2
   Otroto quench
3. 3
   Otrothe reaction
4. 4
   OtroThe aqueous layer was separated
5. 5
   Extracciónextracted with ethyl acetate (3×30 mL)
6. 6
   Lavadowashed with water (30 mL) and brine (30 mL)
7. 7
   Secadodried over Na2SO4
8. 8
   ConcentraciónThe filtrate was concentrated in vacuo
9. 9
   Otroto yield a crude brown solid
10. 10
    OtroA sample of the crude brown solid was purified by column chromatography (SiO2; 100% CH2Cl2)

Procedimiento

4,5-Dichloro-benzene-1,2-diamine (2.03 g; 11.5 mmoles) and 2,3,3,3-tetrafluoro-propionic acid (1.99 g; 13.6 mmoles) were suspended in 6N HCl (5 mL; 30 mmoles) under a nitrogen atmosphere. The reaction was stirred vigorously and heated to 108° C. for 18 hrs, then cooled to room temperature. The reaction was diluted with water (60 mL) and with ethyl acetate (60 mL), then sodium bicarbonate (4.02 g; 47.9 mmoles) was added slowly and in portions to quench the reaction. The aqueous layer was separated and extracted with ethyl acetate (3×30 mL). The extracts were combined, washed with water (30 mL) and brine (30 mL), then dried over Na2SO4. The filtrate was concentrated in vacuo to yield a crude brown solid. A sample of the crude brown solid was purified by column chromatography (SiO2; 100% CH2Cl2) to yield the title compound as a light orange solid.

Fuente