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Acetonitrile → 2-Chloro-1-[2-hydroxy-2-methyl-3-(4-methylbenzenesulfonyloxy)propyl]-4-nitroimidazole

HRID 856148
Notes
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Reaction equation

HRID 856148 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([CH3:25])[CH:15]=[CH:14][C:13]([S:16]([O:19][CH2:20][C:21]2([CH3:24])[CH2:23][O:22]2)(=[O:18])=[O:17])=[CH:12][CH:11]=1.C(#N)C>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(OCC)(=O)C>[Cl:1][C:2]1[N:3]([CH2:24][C:21]([OH:22])([CH3:23])[CH2:20][O:19][S:16]([C:13]2[CH:14]=[CH:15][C:10]([CH3:25])=[CH:11][CH:12]=2)(=[O:18])=[O:17])[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 142371942-Methyloxiran-2-ylmethyl paratoluenesulfonateHCID 178526855HCID 178526855, compound

Product 1

HCID 230812352-Chloro-1-[2-hydroxy-2-methyl-3-(4-methylbenzenesulfonyloxy)propyl]-4-nitroimidazoleYield 70.4%

Reagents, catalysts & solvents 2

HCID 66133
Benzyl triethylammonium chloride
Catalyst
HCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-4-nitro-1H-imidazole (1 g, 6.78 mmol), 2-methyloxiran-2-ylmethyl paratoluenesulfonate (2.46 g, 10.15 mmol), benzyl(triethyl) ammonium chloride (1.50 mg, 0.66 mmol) and acetonitrile (10 ml) were stirred under reflux for 8 hours. The reaction mixture was allowed to return to room temperature, diluted with ethyl acetate. The organic phase was washed with a saturated aqueous sodium bicarbonate solution twice, 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/ethyl acetate=6/1) to afford 2-chloro-1-[2-hydroxy-2-methyl-3-(4-methylbenzenesulfonyloxy)propyl]-4-nitroimidazole (1.86 g, yield 70%) as a light yellow oil.

Workup

  1. temperatureunder reflux for 8 hours
  2. customto return to room temperature
  3. washThe organic phase was washed with a saturated aqueous sodium bicarbonate solution twice
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=6/1)

Sources & evidence

ORD record
ord-85e5f5d25b5d41e995d867a0fdf0182f
Source dataset
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07262212B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes