Ethanol → HCID 178525051, compound

HRID 1612512Notes

Reaction equation

HRID 1612512 reaction equation
[OH-:1].[Li+].[N+:3]([C:6]1[N:7]=[C:8]([C:11]([CH:13]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21]C=2)C(OCC)=O)=O)[NH:9][CH:10]=1)([O-:5])=[O:4].O.[CH2:26]([OH:28])C>>[N+:3]([C:6]1[N:7]=[C:8]([CH:11]([C:13]2[CH:19]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:26]([OH:28])=[O:1])[NH:9][CH:10]=1)([O-:5])=[O:4]

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 3939Lithium HydroxideHCID 178472195HCID 178472195, compound

Product 1

HCID 178525051HCID 178525051, compoundYield 96%

Conditions

Temperature
12 °C

Procedure

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)

Workup

  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

Sources & evidence

ORD record
ord-308a3831ff2c446e9b8cd917bb960788
Source dataset
uspto-grants-2006_01
Patent number
US06992097B2

Reaction notes

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