Isopropanol → 2-Bromo-4-nitro-1H-imidazole

A mixture consisting of 2-bromo-5-iodo-4-nitroimidazole (2.43 g, 7.64 mmol), isopropyl alcohol (12.2 ml), water (2.4 ml), triethylamine (2.32 g, 22.9 mmol), and 5% Pd-alumina (12.2 mg) was stirred while applying pressure (3 to 4 atmospheres) in a hydrogen atmosphere at 60° C. for 3 hours. The filtrate was concentrated and exsiccated under reduced pressure, and the resultant product was then dissolved in water (10 ml). The thus obtained solution was treated with activated carbon (243 mg) (which was stirred at room temperature for 1 hour). The filtrate was stirred under cooling on ice, and 35% concentrated hydrochloric acid (0.7 ml) was added thereto such that the pH of the solution became 2. The thus obtained solution was further stirred under cooling on ice for 1 hour. Thereafter, the precipitated crystals were collected by filtration and then dried at 50° C. for 16 hours.

1. customat 60° C.
2. customfor 3 hours
3. concentrationThe filtrate was concentrated
4. dissolutionthe resultant product was then dissolved in water (10 ml)
5. additionThe thus obtained solution was treated with activated carbon (243 mg) (which was stirred at room temperature for 1 hour)
6. stirringThe filtrate was stirred
7. temperatureunder cooling on ice, and 35% concentrated hydrochloric acid (0.7 ml)
8. additionwas added
9. stirringThe thus obtained solution was further stirred
10. temperatureunder cooling on ice for 1 hour
11. filtrationThereafter, the precipitated crystals were collected by filtration
12. customdried at 50° C. for 16 hours

ORD record

ord-8e1ec6582e12408c861120fc21229b79

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07569702B2