Reaktion #165719

Reaktionsgleichung

3-(chloromethyl)furan

solution

5-chloro-2-methoxy-N-(5-methylthiazol-2-yl)benzamide

sodium hydride

→

title compound

Ausbeute 18.2%

5-chloro-N-[(2Z)-3-(3-furylmethyl)-5-methyl-1,3-thiazol-2(3H)-ylidene]-2-methoxybenzamide

Ausbeute 18.2%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITThe reaction was held at ambient temperature overnight
2. 2
   Sonstigequenched with water
3. 3
   ExtraktionThe crude was extracted with ethyl acetate
4. 4
   Waschenthe organics washed with water
5. 5
   Trocknendried over MgSO4
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated

Vorschrift

To a solution of Example 340A (0.15 g, 0.53 mmol) in 5 mL DMF was added sodium hydride (0.016 g, 0.67 mmol, 95%). After the solution was allowed to stir at ambient temperature for 30 min, 3-(chloromethyl)furan (0.08 g, 0.67 mmol) was added. The reaction was held at ambient temperature overnight and then quenched with water. The crude was extracted with ethyl acetate and the organics washed with water, then dried over MgSO4, filtered, and concentrated. Flash chromatography over silica gel (50% ethyl acetate/hexane) gave 0.035 g of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 2.27 (d, J=1.36 Hz, 3H) 3.80 (s, 3H) 5.38 (s, 2H) 6.39-6.55 (m, 2H) 7.12 (d, J=8.82 Hz, 1H) 7.26 (d, J=1.36 Hz, 1H) 7.46 (dd, J=8.82, 2.71 Hz, 1H) 7.64 (s, 1H) 7.75 (d, J=2.71 Hz, 1H). m/z 363.0 (M+H)+.

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