Furan, 2-(bromomethyl)tetrahydro- → 5-methyl-3-((tetrahydrofuran-2-yl)methyl)thiazol-2(3H)-imine

HRID 78448

Reaktionsgleichung

Reaktionsgleichung von HRID 78448
[NH2:1][C:2]1[S:3][C:4]([CH3:7])=[CH:5][N:6]=1.Br[CH2:9][CH:10]1[CH2:14][CH2:13][CH2:12][O:11]1>>[CH3:7][C:4]1[S:3][C:2](=[NH:1])[N:6]([CH2:9][CH:10]2[CH2:14][CH2:13][CH2:12][O:11]2)[CH:5]=1

Komponenten

3

Edukt 2

HCID 14501Furan, 2-(bromomethyl)tetrahydro-HCID 3517702-Amino-5-methylthiazole

Produkt 1

HCID 668516985-methyl-3-((tetrahydrofuran-2-yl)methyl)thiazol-2(3H)-imineAusbeute 86,2 %

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A mixture of 2-amino-5-methylthiazole (1.0 g, 8.7 mmol) and 2-(bromomethyl)tetrahydrofuran (Maybridge, 1.1 mL, 10 mmol) was warmed to 85° C. and allowed to stir for 24 hours. The mixture was then cooled to ambient temperature and purified via column chromatography (SiO2, 9:1:0.1 CH2Cl2:CH3OH:NH4OH) to afford the title compound (1.5 g, 7.5 mmol, 86% yield). 1H NMR (300 MHz, CD3OD) δ ppm 1.55-1.70 (m, 1H) 1.89-2.01 (m, 2H) 2.07-2.20 (m, 1H) 2.28 (d, J=1.36 Hz, 3H) 3.72-3.82 (m, 1H) 3.86-4.00 (m, 2H) 4.08-4.24 (m, 2H) 6.98-7.04 (m, 1H); MS (DCI/NH3) m/z 199 (M+H)+.

Aufarbeitung

  1. temperatureThe mixture was then cooled to ambient temperature
  2. custompurified via column chromatography (SiO2, 9:1:0.1 CH2Cl2:CH3OH:NH4OH)

Quellen und Nachweise

ORD-Eintrag
ord-733cf708cbff48fc82a0a3de3d0628e0
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841334B2

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