Water → 3-[3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl]-3H-benzoxazol-2-one

HRID 856354Notes

Reaction equation

HRID 856354 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[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[O:17][C:16]2=[O:24])[CH2:13][O:12]1.C([O-])(=O)C.[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[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[O:17][C:16]2=[O:24])[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 517045Sodium AcetateHCID 230815373-(2-methyl-2-oxiranylmethyl)-3H-benzoxazol-2-oneHCID 178526855HCID 178526855, compound

Product 1

HCID 694798443-[3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl]-3H-benzoxazol-2-oneYield 51.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 2-chloro-4-nitro-1H-imidazole (503 mg, 3.41 mmol), 3-(2-methyloxiran-2-yl-methyl)-3H-benzoxazol-2-one (700 mg, 3.41 mmol) in ethanol (7 ml), sodium acetate (336 mg, 4.1 mmol) was added followed by stirring under reflux for 8 hours. The reaction mixture was allowed to return to room temperature. To a mixture, water was added, and the resulting solution was extracted with methylene chloride. The organic phase was dried over magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride/methanol=30/1) to afford 3-[3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl]-3H-benzoxazol-2-one (616 mg, yield 51%) as a light yellow powder.

Workup

  1. additionwas added
  2. temperatureunder reflux for 8 hours
  3. customto return to room temperature
  4. extractionthe resulting solution was extracted with methylene chloride
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (methylene chloride/methanol=30/1)

Sources & evidence

ORD record
ord-efbbc6da6c2f4a0e9fa240cb75b8683d
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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