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Potassium Carbonate → 2,2-dimethyl-5-fluoromethyl-5-[(2-nitro-1H-imidazol-1-yl)methyl]-1,3-dioxane

HRID 514620
Notes
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Reaction equation

HRID 514620 reaction equation
[CH3:1][C:2]1([CH3:29])[O:7][CH2:6][C:5]([CH2:20][N:21]2[CH:25]=[CH:24][N:23]=[C:22]2[N+:26]([O-:28])=[O:27])([CH2:8]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:4][O:3]1.C1N2CCOCCOCCN(CCOCCOCC2)CCOCCOC1.[F-:56].[K+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:1][C:2]1([CH3:29])[O:7][CH2:6][C:5]([CH2:8][F:56])([CH2:20][N:21]2[CH:25]=[CH:24][N:23]=[C:22]2[N+:26]([O-:28])=[O:27])[CH2:4][O:3]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 728012,2,2-CryptandHCID 522689Potassium FluorideHCID 89472102HCID 89472102, compound

Product 1

HCID 894722902,2-dimethyl-5-fluoromethyl-5-[(2-nitro-1H-imidazol-1-yl)methyl]-1,3-dioxaneYield 48.2%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Conditions

Temperature
25 °C

Procedure

30 mg (0.0705 mmol equivalents) of 2,2-dimethyl-5-[(2-nitro-1H-imidazol-1-yl)methyl]-5-(p-toluenesulfonyloxymethyl)-1,3-dioxane was dissolved in 1.0 mL of acetonitrile, 39.8 mg (0.106 mmol equivalents) of Kryptofix 222 (trade name, Merck), 5.1 mg (0.088 mmol equivalents) of potassium fluoride, and 2.0 mg (0.014 mmol equivalents) of potassium carbonate were added thereto, and the mixture was stirred under reflux by heating for 3 hours. After completion of the reaction, the reaction liquid was cooled to room temperature (25° C.), the solvent was then removed by distillation, and the obtained crude product was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=2/1) to give 9.2 mg (0.034 mmol equivalents) of 2,2-dimethyl-5-fluoromethyl-5-[(2-nitro-1H-imidazol-1-yl)methyl]-1,3-dioxane.

Workup

  1. temperatureunder reflux
  2. temperatureby heating for 3 hours
  3. customAfter completion of the reaction
  4. customthe reaction liquid
  5. customthe solvent was then removed by distillation
  6. customthe obtained crude product
  7. customwas purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=2/1)

Sources & evidence

ORD record
ord-d879485147614645b6791ae16e220054
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09107964B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes