Acetone → HCID 86729995, compound

HRID 2199772Notes

Reaction equation

HRID 2199772 reaction equation
[N+:1]([C:4]1[N:5]=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].CC(C)=O.[CH3:19][O:20][CH2:21]Cl>C(OCC)(=O)C.O>[CH3:19][O:20][CH2:21][N:7]1[CH:8]=[C:4]([N+:1]([O-:3])=[O:2])[N:5]=[N:6]1

Participants

7

Reactant 4

HCID 180AcetoneHCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 178526868HCID 178526868, compound

Product 1

HCID 86729995HCID 86729995, compoundYield 61.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-nitro-1H-1,2,3-triazole (6.468 g, 56.707 mmol) and potassium carbonate (15.683 g, 113.472 mmol) were added into 150 mL acetone. Chloromethyl methyl ether (4.74 mL, 62.407 mmol) was added dropwise into the above mixture under ice bath. After completion, water and ethyl acetate were added into the reaction solution. Phases were separated. The aqueous phase was extracted with ethyl acetate. The organic phases were combined, washed with saturated sodium chloride, dried over anhydrous sodium sulfate, filtered, concentrated, chromatographed on a silica gel column (ethyl acetate:petroleum ether=1:5) to obtain 1-(methoxymethyl)-4-nitro-1H-1,2,3-triazole, as 5.517 g of a light yellow liquid, at a yield of 61.5%.

Workup

  1. customPhases were separated
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. washwashed with saturated sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed on a silica gel column (ethyl acetate:petroleum ether=1:5)

Sources & evidence

ORD record
ord-a8029c0094134a6c8282c335b00237fb
Source dataset
uspto-grants-2016_06
Patent number
US09359344B2

Reaction notes

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