Triethylamine → N-Methyl-N-(2-nitrooxyethyl)-2-oxothiazolidine-4-carboxamide monohydrate

HRID 487949

Reaktionsgleichung

Reaktionsgleichung von HRID 487949
C(N(CC)CC)C.[O:8]=[C:9]1[NH:13][CH:12]([C:14]([OH:16])=O)[CH2:11][S:10]1.Cl.CN(CCCN=C=NCC)C.[N+]([O-])(O)=O.[CH3:33][NH:34][CH2:35][CH2:36][O:37][N+:38]([O-:40])=[O:39]>CN(C)C=O>[OH2:8].[CH3:33][N:34]([CH2:35][CH2:36][O:37][N+:38]([O-:40])=[O:39])[C:14]([CH:12]1[CH2:11][S:10][C:9](=[O:8])[NH:13]1)=[O:16]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 652722-Oxo-1,3-thiazolidine-4-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86747699N-methyl-N-(2-nitrooxyethyl)amine nitrate

Produkt 1

HCID 18961052N-Methyl-N-(2-nitrooxyethyl)-2-oxothiazolidine-4-carboxamide monohydrateAusbeute 5,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

0.95 ml of triethylamine, 1.0 g of 2-oxothiazolidine-4-carboxylic acid and 1.30 g of 1-(N,N-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were added, whilst ice-cooling and stirring, to a suspension of 1.24 g of N-methyl-N-(2-nitrooxyethyl)amine nitrate in 50 ml of dry N,N-dimethylformamide, and the resulting mixture was stirred at room temperature for 45 minutes, 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 and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure. The residual yellow oil was purified by column chromatography through silica gel, using a 4:1 by volume mixture of methylene chloride and ethyl acetate as the eluent. The colorless oil thus obtained was triturated with a small amount of tetrahydrofuran to induce crystallization. The crystals which precipitated were collected by filtration and recrystallized from acetone, to give 50 mg of the title compound as colorless crystals, melting at 110°-112° C.

Aufarbeitung

  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 materialdried over anhydrous magnesium sulfate
  6. customThe solvent was then removed by distillation under reduced pressure
  7. customThe residual yellow oil was purified by column chromatography through silica gel
  8. additionby volume mixture of methylene chloride and ethyl acetate as the eluent
  9. customThe colorless oil thus obtained
  10. customwas triturated with a small amount of tetrahydrofuran
  11. customcrystallization
  12. customThe crystals which precipitated
  13. filtrationwere collected by filtration
  14. customrecrystallized from acetone

Quellen und Nachweise

ORD-Eintrag
ord-dc12bde0edd44999876c7286968b8c71
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05298516

Verknüpfte Notizen

Wird geladen…