Diphenyl carbonate → HCID 15839956, compound

HRID 1079446Notes

Reaction equation

HRID 1079446 reaction equation
C(N(CC)CC)C.[C:8](=[O:23])([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)OC1C=CC=CC=1.[N+]([O-])(O)=O.[O:28]([CH2:32][CH2:33][NH2:34])[N+:29]([O-:31])=[O:30]>C(#N)C>[O:28]([CH2:32][CH2:33][NH:34][C:8](=[O:23])[O:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[N+:29]([O-:31])=[O:30]

Participants

5

Reactant 3

HCID 7597Diphenyl carbonateHCID 8471TriethylamineHCID 78397Ethanol, 2-amino-, 1-nitrate, nitrate (1:1)

Product 1

HCID 15839956HCID 15839956, compoundYield 41.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.4 ml of triethylamine was added to a suspension of 0.5 g of diphenyl carbonate and 0.4 g of 2-nitroxyethylamine nitrate in 10 ml of acetonitrile. The mixture was stirred at room temperature for 2 hours and was then allowed to stand overnight at room temperature. The solvent was distilled off under reduced pressure, water was added to the residue, and it was extracted with ethyl acetate 3 times. The extracts were dried over magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography through silica gel (eluent; hexane: ethyl acetate=5:1) to give 0.22 g of the title compound as colorless powdery crystals.

Workup

  1. waitto stand overnight at room temperature
  2. distillationThe solvent was distilled off under reduced pressure, water
  3. additionwas added to the residue, and it
  4. extractionwas extracted with ethyl acetate 3 times
  5. dry with materialThe extracts were dried over magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by column chromatography through silica gel (eluent; hexane: ethyl acetate=5:1)

Sources & evidence

ORD record
ord-2361c47f107e46c88c5acc853c99c67d
Source dataset
uspto-grants-1996_12
Patent number
US05580893

Reaction notes

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