Water → 5-Hydroxymethyl-2-(2-methylpropyl)thiazole

HRID 14054

Reaktionsgleichung

Reaktionsgleichung von HRID 14054
[C:1](=[S:7])([NH2:6])[CH2:2][CH:3]([CH3:5])[CH3:4].[CH:8]([CH:10](Cl)[C:11](OCC)=O)=[O:9].O.C(=O)(O)[O-].[Na+]>CN(C=O)C>[OH:9][CH2:8][C:10]1[S:7][C:1]([CH2:2][CH:3]([CH3:5])[CH3:4])=[N:6][CH:11]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 118030Ethyl (chloroformyl)acetateHCID 516892Sodium BicarbonateHCID 3034257Butanethioamide, 3-methyl-

Produkt 1

HCID 210859775-Hydroxymethyl-2-(2-methylpropyl)thiazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

Isovalerothioamide (6.0 g, 51 mmol) and ethyl formylchloroacetate (Heterocycles 32 (4), 693-701, (1991), 5.0 g, 33 mmol) are dissolved in dry DMF (20 mL), and heated to 95 degrees C. for 4 hours. The reaction is subsequently cooled to 0 degrees C., and cold water (50 mL) is added. The mixture is basified to pH=8 with solid sodium bicarbonate, then extracted with ether (3×35 mL). The combined organic extracts are washed with water, then saline and dried over magnesium sulfate, filtered, and concentrated. The residue is purified by flash chromatography (ethyl acetate/hexanes 4-10% elution) to give the desired product. NMR (CDCl3, 300 MHz) δ 8.27, 4.45-4.30, 3.70-3.50, 3.00-2.80, 2.30-2.10, 1.40-1.20, and 1.10-0.90.

Aufarbeitung

  1. temperatureThe reaction is subsequently cooled to 0 degrees C
  2. extractionextracted with ether (3×35 mL)
  3. washThe combined organic extracts are washed with water
  4. dry with materialsaline and dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified by flash chromatography (ethyl acetate/hexanes 4-10% elution)

Quellen und Nachweise

ORD-Eintrag
ord-75f58f65667748a0a0f97a393217bc0e
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727997B2

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