Triethylamine → HCID 18961076, compound

HRID 1708181Notes

Reaction equation

HRID 1708181 reaction equation
C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N.[N+]([O-])(O)=O.[N+:22]([O:25][CH2:26][CH2:27][NH2:28])([O-:24])=[O:23].[CH3:29][N:30]1[CH:34]([C:35](O)=[O:36])[CH2:33][S:32][C:31]1=[O:38]>O1CCCC1>[N+:22]([O:25][CH2:26][CH2:27][NH:28][C:35]([CH:34]1[CH2:33][S:32][C:31](=[O:38])[N:30]1[CH3:29])=[O:36])([O-:24])=[O:23]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 78397Ethanol, 2-amino-, 1-nitrate, nitrate (1:1)HCID 18961027HCID 18961027, compound

Product 1

HCID 18961076HCID 18961076, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.33 ml of triethylamine and 0.36 ml of diethyl cyanophosphonate were added, whilst ice-cooling and stirring, to a suspension of 402 mg of N-(2-nitrooxyethyl)amine nitrate and 326 mg of 3-methyl-2-oxothiazolidine-4-carboxylic acid in 35 ml of dry tetrahydrofuran, and the resulting mixture was stirred at room temperature for 3.5 hours, after which the solvent was removed by distillation under reduced pressure. The residue was mixed with ethyl acetate, and the resulting mixture was washed with a saturated aqueous solution of sodium chloride. It was then dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The crystalline residue was recrystallized from ethanol, to give 247 mg of the title compound as colorless crystals, melting at 105°-106° C.

Workup

  1. temperaturecooling
  2. customafter which the solvent was removed by distillation under reduced pressure
  3. additionThe residue was mixed with ethyl acetate
  4. washthe resulting mixture was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialIt was then dried over anhydrous magnesium sulfate
  6. customthe solvent was removed by distillation under reduced pressure
  7. customThe crystalline residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-a1d74b58ce25434db560880e2e168b69
Source dataset
uspto-grants-1994_10
Patent number
US05356918

Reaction notes

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