Réaction #9679

Équation de réaction

1,2-Diamino-5-trifluoromethylbenzene

4-bromo-2-fluoro-phenylisothiocyanate

1,3-dicyclohexylcarbodiimide

→

N-(4-Bromo-2-fluorophenyl)-N-[5-(trifluoromethyl)-1H-benzimidazol-2-yl]amine

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction was heated in a 45° C. oil bath overnight
2. 2
   Températurecooled
3. 3
   Concentrationconcentrated at reduced pressure
4. 4
   workup.ADDITIONThe dark residue was diluted with ethyl acetate
5. 5
   Lavagethe organic layer was washed with water
6. 6
   SéchageThe organic layer was dried (MgSO4)
7. 7
   Concentrationconcentrated in vacuo
8. 8
   AutreThe resulting dark brown oil was purified by flash chromatography on silica gel
9. 9
   Lavageeluted on a gradient from 9:1 hexanes/ethyl acetate to 100% ethyl acetate
10. 10
    AutreThe title compound was collected as a light pink solid (0.60 g, 57%)

Mode opératoire

1,2-Diamino-5-trifluoromethylbenzene (0.50 g, 2.84 mmol) was diluted in dichloromethane (5 mL) and treated with 4-bromo-2-fluoro-phenylisothiocyanate (0.66 g, 2.84 mmol). The dark solution was stirred at 45° C. for 15 minutes, then 1,3-dicyclohexylcarbodiimide (0.44 g, 2.13 mmol) was added all at once. The reaction was heated in a 45° C. oil bath overnight, then cooled and concentrated at reduced pressure. The dark residue was diluted with ethyl acetate, and the organic layer was washed with water. The organic layer was dried (MgSO4) and concentrated in vacuo. The resulting dark brown oil was purified by flash chromatography on silica gel eluted on a gradient from 9:1 hexanes/ethyl acetate to 100% ethyl acetate. The title compound was collected as a light pink solid (0.60 g, 57%). 1H NMR (300 MHz, DMSO-d6) δ 11.3 (broad d, 1H), 9.87 (d, 1H), 7.50 (d, 2H), 7.61 (d, 1H), 7.55–7.41 (m, 3H), 7.35–7.30 (m, 1H); LC/MS m/z 356.2 (MH+), retention time 2.33 minutes.

Source