Hydrochloric Acid → 5,6-Dichloro-2-(1,2,2,2-tetrafluoroethyl)-1H-benzimidazole

Temperature

108 °C

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.

1. temperaturecooled to room temperature
2. customto quench
3. customthe reaction
4. customThe aqueous layer was separated
5. extractionextracted with ethyl acetate (3×30 mL)
6. washwashed with water (30 mL) and brine (30 mL)
7. dry with materialdried over Na2SO4
8. concentrationThe filtrate was concentrated in vacuo
9. customto yield a crude brown solid
10. customA sample of the crude brown solid was purified by column chromatography (SiO2; 100% CH2Cl2)

ORD record

ord-08ff032ec1d34173ae2507ac0ae3d0fa

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07879895B2