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

반응식

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

참가 물질

반응물 3

HCID 887Methanol

HCID 732294-Chloromethylthiazol-2-ylamine

HCID 2724254Sodium bis(trimethylsilyl)amide

생성물 1

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

실험 절차

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%).