Triethylamine → HCID 15839957, compound

HRID 1079447Notes

Reaction equation

HRID 1079447 reaction equation
C(N(CC)CC)C.P(C#N)(OCC)(OCC)=O.[O:18]([CH2:25][C:26]([OH:28])=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[N+]([O-])(O)=O.[O:33]([CH2:37][CH2:38][NH2:39])[N+:34]([O-:36])=[O:35]>O1CCCC1>[O:33]([CH2:37][CH2:38][NH:39][C:26](=[O:28])[CH2:25][O:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[N+:34]([O-:36])=[O:35]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 19188Phenoxyacetic AcidHCID 76257Diethyl cyanophosphonateHCID 78397Ethanol, 2-amino-, 1-nitrate, nitrate (1:1)

Product 1

HCID 15839957HCID 15839957, compoundYield 31.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.5 ml of triethylamine and 0.7 ml of diethyl cyanophosphate were added to a suspension of 0.65 g of phenoxyacetic acid and 0.6 g of 2-nitroxyethylamine nitrate in 20 ml of tetrahydrofuran with ice-cooling. The mixture was stirred at room temperature for 2 hours and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography through silica gel (eluent; hexane: ethyl acetate=1:1) and then recrystallized from diisopropyl ether to give 0.27 g of the title compound as colorless needles.

Workup

  1. temperaturecooling
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe residue was purified by column chromatography through silica gel (eluent; hexane: ethyl acetate=1:1)
  4. customrecrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-8e29b84cb7e54508a3ddecd8d78f6c8e
Source dataset
uspto-grants-1996_12
Patent number
US05580893

Reaction notes

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