Ethanol → HCID 178525051, compound

Temperature

12 °C

Lithium hydroxide (18.1 g, 750 mm, 2 eq) was added to a stirred slurry of ethyl 2-(4-nitroimidazoyl)-2-phenylacetate (Preparation 11 from Examples Part 1) (104 g, 379 mm) in 250 mL of ethanol. Deionized water was added to the resulting mixture and the stirring was continued for 4 hours. The ethanol was removed under vacuum and the resulting aqueous solution was washed with 100 mL of diethyl ether. The aqueous layer was diluted with 100 mL of deionized water and the pH was adjusted to 1.8 with concentrated HCl after cooling to 12° C. The resulting slurry was stirred for 30 minutes at less than 5 degrees and filtered. The wet cake was washed with 100 mL of deionized water and dried under a stream of air on the filter overnight to yield 90.34 g (96%) of a brown solid. The product may be recrystallized from isopropyl alcohol to give 72.31 g (80% recovery, 77% overall yield) of a tan solid. Elemental analysis: Calculated: %C, 53.45; %H, 3.67; %N, 16.97. Found: : %C, 53.67; %H, 3.79; %N, 16.65. MS: 247 (M+): IR (cm−1)1719; H1 nmr (d6 DMSO): d 6.51 (s, 1H), 7.43-7.55 (m, 5H), 7.95 (s, 1H), 8.40 (s, 1H).

1. customThe ethanol was removed under vacuum
2. washthe resulting aqueous solution was washed with 100 mL of diethyl ether
3. additionThe aqueous layer was diluted with 100 mL of deionized water
4. filtrationfiltered
5. washThe wet cake was washed with 100 mL of deionized water
6. customdried under a stream of air on the filter overnight

ORD record

ord-8017db35e3084a68bd7805677413b3b8

Source dataset

uspto-grants-2003_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06639076B1