Nitric Acid → 2-Ethyl-4-methyl-5-(2-nitrooxy-ethyl)-thiazole

HRID 1094826

Reaktionsgleichung

Reaktionsgleichung von HRID 1094826
[N+:1]([O-:4])([OH:3])=[O:2].S(=O)(=O)(O)O.[CH2:10]([C:12]1[S:13][C:14]([CH2:18][CH2:19]O)=[C:15]([CH3:17])[N:16]=1)[CH3:11].[OH-].[Na+]>CCCCCC.O>[CH2:10]([C:12]1[S:13][C:14]([CH2:18][CH2:19][O:2][N+:1]([O-:4])=[O:3])=[C:15]([CH3:17])[N:16]=1)[CH3:11]

Komponenten

7

Edukt 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 184408242-(2-Ethyl-4-methyl-thiazol-5-yl)-ethanol

Produkt 1

HCID 116871642-Ethyl-4-methyl-5-(2-nitrooxy-ethyl)-thiazoleAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
2.5 °C

Versuchsvorschrift

Fifteen (15) ml of nitric acid of (85-90%) were added dropwise to 15 ml of sulfuric acid (95-98%) over a time period of 20 minutes while keeping the temperature at 0-5° C. After 2 hours, 14.3 grams (83.60 mmol) of 2-ethyl-4-methyl-5-thiazoleethanol, prepared as described above, were added, while the temperature was still maintained at 0-5° C., the reaction mixture was stirred for 2 hours at the same temperature, and was then poured carefully onto 125 ml of cold water. The water solution was made basic with a 20% aqueous solution of sodium hydroxide and the aqueous phase was extracted with three portions of 75 grams of dichloromethane. The extracts were combined and dried over sodium sulfate, filtered and evaporated to dryness. Chromatography of the crude product on silica gel (using a mixture of 75:25 ethyl acetate:hexane as an eluent) yielded 10.5 grams (58% yield) of colorless liquid having a purity of 98%, as determined by gas chromatography.

Aufarbeitung

  1. customat 0-5° C
  2. additionwere added, while the temperature
  3. extractionthe aqueous phase was extracted with three portions of 75 grams of dichloromethane
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. additiona mixture of 75:25 ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-52a779a2a4224834a9e71c53a830475c
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08134010B2

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