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Hydrochloric Acid → 1-(4-Methyl-2-thiazolyl)-2-(2-chloroethoxy)ethanol

HRID 1198276
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1198276
[CH3:1][C:2]1[N:3]=[C:4]([CH:7]=[O:8])[S:5][CH:6]=1.[Cl:9][CH2:10][CH2:11][O:12][CH2:13][Mg]Cl.[Cl-].[NH4+].Cl.C(=O)([O-])O.[Na+]>O1CCCC1.C(OCC)(=O)C>[CH3:1][C:2]1[N:3]=[C:4]([CH:7]([OH:8])[CH2:13][O:12][CH2:11][CH2:10][Cl:9])[S:5][CH:6]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 42634324-Methyl-1,3-thiazole-2-carbaldehydeHCID 178478511HCID 178478511, Verbindung

Produkt 1

HCID 538501531-(4-Methyl-2-thiazolyl)-2-(2-chloroethoxy)ethanol

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
-30 °C

Versuchsvorschrift

1.6 g of 4-methyl-2-formylthiazole was dissolved in 30 ml of tetrahydrofuran. The solution was cooled to -30° C. Thereto was dropwise added, in 10 minutes, 10 ml of a tetrahydrofuran solution containing 1.6M of 2-chloroethoxymethylmagnesium chloride. The mixture was stirred for 1 hour with ice cooling. The reaction mixture was added to a mixture of 50 ml of ice water, 50 ml of ethyl acetate and 2 g of ammonium chloride. The resulting mixture was adjusted to pH 2 with 6N hydrochloric acid and stirred at the same temperature for 5 minutes. The reaction mixture was adjusted to pH 6 with a saturated aqueous sodium hydrogencarbonate solution. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue thus obtained was purified by column chromatography (eluant: toluene/ethyl acetate=4/1) to obtain 1.3 g of oily 1-(4-methyl-2-thiazolyl)-2-(2-chloroethoxy)ethanol.

Aufarbeitung

  1. additionThereto was dropwise added, in 10 minutes
  2. stirringstirred at the same temperature for 5 minutes
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  6. customThe solvent was removed by distillation under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified by column chromatography (eluant: toluene/ethyl acetate=4/1)

Quellen und Nachweise

ORD-Eintrag
ord-d5855472080c4d82849060da602f7091
Quelldatensatz
uspto-grants-1994_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05280032

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