Sodium Acetate → HCID 23081189, compound

HRID 856165Notes

Reaction equation

HRID 856165 reaction equation
[Cl:1][C:2]1[NH:3][CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[C:10]([O:13][CH2:14][CH2:15][CH2:16][C:17]1([CH3:20])[CH2:19][O:18]1)(=[O:12])[CH3:11].C([O-])(=O)C.[Na+]>C(O)C>[Cl:1][C:2]1[N:3]([CH2:20][C:17]([OH:18])([CH3:19])[CH2:16][CH2:15][CH2:14][O:13][C:10](=[O:12])[CH3:11])[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 13616676HCID 13616676, compoundHCID 178526855HCID 178526855, compound

Product 1

HCID 23081189HCID 23081189, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chloro-4-nitro-1H-imidazole (6.8 g, 43 mmol), 2-(3-acetoxypropyl)-2-methyloxirane (5.8 g, 39.3 mmol) and sodium acetate (3.9 g, 47.6 mmol) were suspended in ethanol (60 ml) followed by stirring under reflux overnight. The reaction mixture was allowed to return to room temperature and concentrated under reduced pressure. Water was added to the residue, and the resulting mixture was extracted with methylene chloride twice. The organic phases were combined, washed with a saturated aqueous sodium bicarbonate solution and a saturated saline solution in this order, dried over sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure to afford 2-chloro-l-(5-acetoxy-2-hydroxy-2-methylpentyl)-4-nitroimidazole (9.5 g, yield 79%) as a light brown oil.

Workup

  1. temperatureunder reflux overnight
  2. customto return to room temperature
  3. concentrationconcentrated under reduced pressure
  4. additionWater was added to the residue
  5. extractionthe resulting mixture was extracted with methylene chloride twice
  6. washwashed with a saturated aqueous sodium bicarbonate solution
  7. dry with materiala saturated saline solution in this order, dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d528ab0391b14d89b4114c242a8dd642
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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