Sodium Acetate → HCID 23081423, compound

HRID 856357Notes

Reaction equation

HRID 856357 reaction equation
[Cl:1][C:2]1[NH:3][CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[C:10]1([C:16]2[CH:17]=[CH:18][C:19]3[O:23][C:22](=[O:24])[N:21]([CH2:25][C:26]4([CH3:29])[CH2:28][O:27]4)[C:20]=3[CH:30]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])(=O)C.[Na+]>C(O)C>[Cl:1][C:2]1[N:3]([CH2:28][C:26]2([CH3:29])[O:27][C:22](=[O:24])[N:21]([C:20]3[CH:30]=[C:16]([C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=4)[CH:17]=[CH:18][C:19]=3[OH:23])[CH2:25]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 23081624HCID 23081624, compoundHCID 178526855HCID 178526855, compound

Product 1

HCID 23081423HCID 23081423, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-chloro-4-nitro-1H-imidazole (1.3 g, 8.78 mmol), 5-phenyl-3-(2-methyloxiran-2-yl-methyl)-3H-benzoxazol-2-one (2.47 g, 8.78 mmol), sodium acetate (792 mg, 9.66 mmol) and ethanol (30 ml) was stirred under reflux for 10 hours. The reaction mixture was allowed to return to room temperature and concentrated under reduced pressure. To the residue, 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=10/1) to afford 5-(2-chloro-4-nitroimidazol-1-ylmethyl)-3-(4-hydroxybiphenyl-3-yl)-5-methyloxazolidin-2-one (1.82 g, yield 61%) as a white powder.

Workup

  1. temperatureunder reflux for 10 hours
  2. customto return to room temperature
  3. concentrationconcentrated under reduced pressure
  4. additionTo the residue, water was added
  5. extractionthe resulting solution was extracted with methylene chloride
  6. dry with materialThe organic phase was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (methylene chloride/methanol=10/1)

Sources & evidence

ORD record
ord-c249665c46674c2480b1edad5be439cc
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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