Potassium Hydroxide → (2-((Dimethylamino)methyl)thiazol-4-yl)methanol

HRID 1075053

Reaktionsgleichung

Reaktionsgleichung von HRID 1075053
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([N:12]([CH2:14][C:15]1[S:16][CH:17]=[C:18]([C:20](OCC)=[O:21])[N:19]=1)[CH3:13])(OCC)=O.[O-]S([O-])(=O)=O.[Na+].[Na+].[OH-].[K+]>O1CCCC1>[CH3:13][N:12]([CH2:14][C:15]1[S:16][CH:17]=[C:18]([CH2:20][OH:21])[N:19]=1)[CH3:7]

Komponenten

6

Edukt 4

HCID 14797Potassium HydroxideHCID 24436Sodium SulfateHCID 204021112-(N-Carbethoxy-N-methylamino)methyl-4-carbethoxythiazoleHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 1838020(2-((Dimethylamino)methyl)thiazol-4-yl)methanolAusbeute 34,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a cooled suspension of lithium aluminum hydride (8.4 g; 0.22 mole) in 80 ml of dry tetrahydrofuran was added a solution of 2-(N-carbethoxy-N-methylamino)methyl-4-carbethoxythiazole (20.0 g; 0.07 mole) [prepared in Step C] in 160 ml of dry tetrahydrofuran over a 1 hour period. The reaction mixture was heated at reflux temperature for 8 hours, then cooled and decomposed with Na2SO4 and 40% aqueous potassium hydroxide. The mixture was filtered, dried and evaporated under reduced pressure to give 4.2 g of the title compound as an oil; TLC (aluminum oxide/CH3CN) gave RF=0.45. The NMR spectrum (60 MHz) in CDCl3 gave the following resonances δ: 7.17 (s, 1H); 4.73 (d, 2H); 3.43 (s, 2H); 3.35 (s, 6H).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux temperature for 8 hours
  3. temperaturecooled
  4. filtrationThe mixture was filtered
  5. customdried
  6. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-66bef489d3354c95bdccadfdb9e3a79c
Quelldatensatz
uspto-grants-1983_07
Patentnummer
US04394508

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