Sodium Acetate → 1-(2-chloro-4-nitroimidazol-1-yl)-2-methyl-3-(1-phenyl-1H-tetrazol-5-ylthio)propane-2-ol

HRID 856177Notes

Reaction equation

HRID 856177 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][S:15][C:16]2[N:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:19]=[N:18][N:17]=2)[CH2:13][O:12]1.C([O-])(=O)C.[Na+]>C(O)C>[Cl:1][C:2]1[N:3]([CH2:10][C:11]([CH3:13])([OH:12])[CH2:14][S:15][C:16]2[N:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:19]=[N:18][N:17]=2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 230815345-(2-methyloxiran-2-ylmethylthio)-1-phenyl-1H-tetrazoleHCID 178526855HCID 178526855, compound

Product 1

HCID 230814071-(2-chloro-4-nitroimidazol-1-yl)-2-methyl-3-(1-phenyl-1H-tetrazol-5-ylthio)propane-2-olYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-chloro-4-nitro-1H-imidazole (1.2 g, 8.13 mmol), 5-(2-methyloxiran-2-ylmethylthio)-1-phenyl-1H-tetrazole (1.9 g, 7.65 mmol), sodium acetate (700 mg, 8.53 mmol) and ethanol (20 ml) was stirred under reflux overnight. The reaction mixture was allowed to return to room temperature and concentrated under reduced pressure. To the residue, water was added, and the resulting mixture was extracted with ethyl acetate twice. The organic phases were combined, washed with a saturated aqueous sodium bicarbonate solution twice, then washed with water and a saturated saline solution in this order, dried over sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/methanol=50/1) to afford 1-(2-chloro-4-nitroimidazol-1-yl)-2-methyl-3-(1-phenyl-1H-tetrazol-5-ylthio)propane-2-ol to afford (2.1 g, yield 69%) as a light yellow powder.

Workup

  1. temperatureunder reflux overnight
  2. customto return to room temperature
  3. concentrationconcentrated under reduced pressure
  4. additionTo the residue, water was added
  5. extractionthe resulting mixture was extracted with ethyl acetate twice
  6. washwashed with a saturated aqueous sodium bicarbonate solution twice
  7. washwashed with water
  8. dry with materiala saturated saline solution in this order, dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (methylene chloride/methanol=50/1)

Sources & evidence

ORD record
ord-1ec0f740d1bf4218b7821c81b041df06
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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