Water → 3-[3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl]-5-(4-trifluoromethoxyphenyl)-3H-[1,3,4]oxadiazol-2-one

HRID 856346Notes

Reaction equation

HRID 856346 reaction equation
[Cl:1][C:2]1[NH:3][CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[CH3:10][C:11]1([CH2:14][N:15]2[N:19]=[C:18]([C:20]3[CH:25]=[CH:24][C:23]([O:26][C:27]([F:30])([F:29])[F:28])=[CH:22][CH:21]=3)[O:17][C:16]2=[O:31])[CH2:13][O:12]1.C(=O)([O-])O.[Na+].O>C(O)C>[Cl:1][C:2]1[N:3]([CH2:13][C:11]([OH:12])([CH3:10])[CH2:14][N:15]2[N:19]=[C:18]([C:20]3[CH:21]=[CH:22][C:23]([O:26][C:27]([F:30])([F:28])[F:29])=[CH:24][CH:25]=3)[O:17][C:16]2=[O:31])[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 230811343-(2-methyl-2-oxiranylmethyl)-5-(4-trifluoromethoxyphenyl)-3H-[1,3,4]oxadiazol-2-oneHCID 178526855HCID 178526855, compound

Product 1

HCID 230815053-[3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl]-5-(4-trifluoromethoxyphenyl)-3H-[1,3,4]oxadiazol-2-oneYield 94.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 2-chloro-4-nitro-1H-imidazole (2.21 g, 14.98 mmol) and 3-(2-methyloxiran-2-ylmethyl)-5-(4-trifluoromethoxyphenyl)-3H-[1,3,4]oxadiazol-2-one (2.37 g, 7.49 mmol) in ethanol (25 ml), sodium hydrogencarbonate (1.32 g, 15.73 mmol) was added followed by stirring under reflux for 8 hours. To the reaction mixture, water was added, and the mixture was extracted with methylene chloride. The organic phase was dried over magnesium sulfate, and concentrated under reduced pressure to afford 3-[3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl]-5-(4-trifluoromethoxyphenyl)-3H-[1,3,4]oxadiazol-2-one (3.27 g, yield 94%) as a light yellow amorphous form.

Workup

  1. additionwas added
  2. temperatureunder reflux for 8 hours
  3. extractionthe mixture was extracted with methylene chloride
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-70e0b178697c42118192ff2ce142dbf4
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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