Dichloromethane → 5-Methyl-3-(tetrahydro-pyran-2-ylmethyl)-3H-thiazol-2-ylideneamine

HRID 1037874

Reaktionsgleichung

Reaktionsgleichung von HRID 1037874
[NH2:1][C:2]1[S:3][C:4]([CH3:7])=[CH:5][N:6]=1.Br[CH2:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][O:11]1.CCOC(C)=O.C(Cl)Cl>CO>[NH4+:1].[OH-:11].[CH3:7][C:4]1[S:3][C:2](=[NH:1])[N:6]([CH2:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][O:11]2)[CH:5]=1

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 1419172-(Bromomethyl)tetrahydro-2H-pyranHCID 3517702-Amino-5-methylthiazole

Produkt 2

HCID 14923Ammonium HydroxideHCID 668596105-Methyl-3-(tetrahydro-pyran-2-ylmethyl)-3H-thiazol-2-ylideneamineAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A mixture of 2-amino-5-methylthiazole (1.2 g, 10.5 mmol) and 2-(bromomethyl)tetrahydro-2H-pyran (Aldrich, 1.5 mL, 11.6 mmol) was warmed to 85° C. and allowed to stir for 18 hours. The mixture was cooled to ambient temperature and purified by flash column chromatography (SiO2, first 10% CH3OH:EtOAc then 9:1:0.1 CH2Cl2:CH3OH:NH4OH) to afford the title compound (1.1 g, 5.2 mmol, 49% yield). 1H NMR (300 MHz, CDCl3) δ ppm 1.12-1.32 (m, 1H) 1.44-1.63 (m, 2H) 1.79-1.95 (m, 2H) 2.06 (d, J 12.89 Hz, 1H) 2.25 (d, J=1.36 Hz, 3H) 3.33-3.45 (m, 1H) 3.65-3.78 (m 1H) 3.86-4.01 (m, 2H) 4.44 (dd, J=14.92, 2.03 Hz, 1H) 6.56-6.65 (m, 1H) 9.48 (s, 1H); MS (DCI/NH3) m/z 213 (M+H)+.

Aufarbeitung

  1. temperatureThe mixture was cooled to ambient temperature
  2. custompurified by flash column chromatography (SiO2, first 10% CH3OH

Quellen und Nachweise

ORD-Eintrag
ord-a4c3345bc13545b6b40de187471926b5
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546583B2

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