Reaktion #165702

Reaktionsgleichung

solution

N-(5-tert-butylthiazol-2-yl)-5-chloro-2-methoxybenzamide

NaH

water

→

title compound

N-[(2Z)-5-tert-butyl-3-(3-hydroxy-3-methylbutyl)-1,3-thiazol-2(3H)-ylidene]-5-chloro-2-methoxybenzamide

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl acetate
2. 2
   WaschenThe organic layer was washed with H2O (2×50 mL)
3. 3
   Trocknendried over MgSO4
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated under reduced pressure
6. 6
   Sonstigedried under vacuum (˜1 mm Hg)

Vorschrift

A solution of Example 244A (75 mg, 0.23 mmol) in N,N-dimethylformamide (2 mL) was treated with NaH 60% dispersion in oil (9.5 mg, 0.23 mmol) followed by Example 308A (60 mg, 0.23 mmol). The reaction mixture was stirred at room temperature for 18 hours, poured into water and extracted with ethyl acetate. The organic layer was washed with H2O (2×50 mL), dried over MgSO4, filtered, concentrated under reduced pressure and dried under vacuum (˜1 mm Hg) to afford the title compound. 1H NMR (300 MHz, dimethylsulfoxide-d6) δ ppm 1.17 (s, 6H), 1.32 (s, 9H), 1.76-1.91 (m, 2H), 3.79 (s, 3H), 4.14-4.31 (m, 2H), 4.43 (s, 1H), 7.10 (d, J=8.8 Hz, 1H), 7.31 (s, 1H), 7.44 (dd, J=9.0, 2.9 Hz, 1H), 7.76 (d, J=3.1 Hz, 1H); MS (ESI) m/z 411 (M+H)h Anal. Calculated for C20H27ClN2O3SC, 58.45; H, 6.62; N, 6.82. Found C, 58.30; H, 6.51; N, 6.71.

Quelle