Methanol → 4-(Methoxymethyl)-1,3-thiazol-2-amine

HRID 20496

Reaktionsgleichung

Reaktionsgleichung von HRID 20496
C[Si](C)(C)[N-][Si](C)(C)C.[Na+].Cl[CH2:12][C:13]1[N:14]=[C:15]([NH2:18])[S:16][CH:17]=1.[CH3:19][OH:20]>>[CH3:19][O:20][CH2:12][C:13]1[N:14]=[C:15]([NH2:18])[S:16][CH:17]=1

Komponenten

4

Edukt 3

HCID 887MethanolHCID 732294-Chloromethylthiazol-2-ylamineHCID 2724254Sodium bis(trimethylsilyl)amide

Produkt 1

HCID 230925274-(Methoxymethyl)-1,3-thiazol-2-amineAusbeute 21 %

Versuchsvorschrift

Sodium hexamethyldisilazide (10M in THF, 0.67 mL, 0.67 mmol) was added to a solution of 4-(chloromethyl)-1,3-thiazol-2-amine (J. Indian Chem. Soc. 1960, 37, 241; 100 mg, 0.67 mmol) in methanol (5 mL) followed by stirring under argon at ambient temperature for 72 h. The solvent was then removed under reduced pressure and the residue was taken up in saturated aqueous sodium hydrogencarbonate (20 mL) and ethyl acetate (50 mL). The organic layer was separated then dried (MgSO4); filtered and evaporated. Purification by column chromatography, eluting with 80% to 100% ethyl acetate in hexanes, afforded the title compound as a colourless oil (20 mg, 21%).

Aufarbeitung

  1. customThe solvent was then removed under reduced pressure
  2. customThe organic layer was separated
  3. dry with materialthen dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by column chromatography
  7. washeluting with 80% to 100% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-7dd8a60206c64f17a3ef8992c5a54d1b
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745475B2

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