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Potassium Carbonate → 4-Carboxy-N-(2,2-dimethyl-3-nitroxypropionyl)-2-phenylthiazolidine

HRID 1770213
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1770213
[CH3:1][C:2]([CH3:11])([CH2:6][O:7][N+:8]([O-:10])=[O:9])[C:3](Cl)=[O:4].[C:12]([CH:15]1[CH2:19][S:18][CH:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[NH:16]1)([OH:14])=[O:13].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.O>[C:12]([CH:15]1[CH2:19][S:18][CH:17]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:16]1[C:3](=[O:4])[C:2]([CH3:11])([CH3:1])[CH2:6][O:7][N+:8]([O-:10])=[O:9])([OH:14])=[O:13]
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Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 392372-Phenylthiazolidine-4-carboxylic acidHCID 200955153-Chloro-2,2-dimethyl-3-oxopropyl nitrate

Produkt 1

HCID 677785314-Carboxy-N-(2,2-dimethyl-3-nitroxypropionyl)-2-phenylthiazolidineAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 5.2 g of 2,2-dimethyl-3-nitroxypropanoyl chloride in 100 ml of tetrahydrofuran was added at 0° C. under nitrogen to a solution of 6.0 g of 4-carboxy-2-phenylthiazolidine and 4.0 g of potassium carbonate in a mixture of 50 ml of tetrahydrofuran and 150 ml of water. After stirring the resulting solution for 45 minutes the mixture was concentrated under reduced pressure to about 150 ml and then acidified to pH=2 with citric acid. The resulting mixture was extracted with diethyl ether and the organic phase was dried over sodium sulphate and evaporated. The residue was purified by chromatography (silica, petroleum ether 60-80: ethyl acetate: acetic acid/8:8:1). Yield 38%. Empirical formula C15H18N2O6S. Molecular weight 354. Melting point 35°-38° C. TLC system: petroleum ether 60-80: ethyl acetate: acetic acid/4:4:1. Rf 0.50.

Aufarbeitung

  1. concentrationwas concentrated under reduced pressure to about 150 ml
  2. extractionThe resulting mixture was extracted with diethyl ether
  3. dry with materialthe organic phase was dried over sodium sulphate
  4. customevaporated
  5. customThe residue was purified by chromatography (silica, petroleum ether 60-80: ethyl acetate: acetic acid/8:8:1)

Quellen und Nachweise

ORD-Eintrag
ord-707e8f9929274e4d80a83760980aa464
Quelldatensatz
uspto-grants-1995_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05385922

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