Triethylamine → N-(2-Nitrooxyethyl)-5-(1-naphthyl)-2-oxothiazolidine-4-carboxamide

HRID 487951Notes

Reaction equation

HRID 487951 reaction equation
C(N(CC)CC)C.[N+]([O-])(O)=O.[N+:12]([O:15][CH2:16][CH2:17][NH2:18])([O-:14])=[O:13].[C:19]1([CH:29]2[S:33][C:32](=[O:34])[NH:31][CH:30]2[C:35](O)=[O:36])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1>O1CCCC1>[N+:12]([O:15][CH2:16][CH2:17][NH:18][C:35]([CH:30]1[CH:29]([C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=[CH:21][CH:20]=2)[S:33][C:32](=[O:34])[NH:31]1)=[O:36])([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 78397Ethanol, 2-amino-, 1-nitrate, nitrate (1:1)HCID 189610635-(1-Naphthyl)-2-oxothiazolidine-4-carboxylic acid

Product 1

HCID 18961030N-(2-Nitrooxyethyl)-5-(1-naphthyl)-2-oxothiazolidine-4-carboxamideYield 55.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.23 ml of triethylamine and 0.36 ml of diethyl cyanosphonate were added, whilst ice-cooling and stirring, to a suspension of 370 mg of N-(2-nitrooxyethyl)amine nitrate and 500 mg of 5-(1-naphthyl)-2-oxothiazolidine-4-carboxylic acid in 50 ml of dry tetrahydrofuran, and the resulting mixture was stirred at room temperature for 4 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, and the residue was mixed with ethyl acetate. The resulting mixture was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, and the crystalline residue was recrystallized from ethanol, to give 367 mg of the title compound as colorless crystals, melting at 151°-153° C.

Workup

  1. temperaturecooling
  2. customAt the end of this time, 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 materialdried over anhydrous magnesium sulfate
  6. customThe solvent was then removed by distillation under reduced pressure
  7. customthe crystalline residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-2163d5d757d64644a116847e938296be
Source dataset
uspto-grants-1994_03
Patent number
US05298516

Reaction notes

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