Réaction #73655

Équation de réaction

Benzhydrazide

4-methylmorpholine

2-benzamido-4-methylthiazole-5-carboxylic acid

N-methylmorpholine

isobutyl chloroformate

→

title compound

Rendement 14.0%

N-(5-(2-Benzoylhydrazinecarbonyl)-4-methylthiazol-2-yl)benzamide

Rendement 14.0%

Solvants

ethyl acetate

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGAfter being stirred at ambient temperature for 18 hours
2. 2
   Lavagewashed with water (3×10 mL)
3. 3
   AutreThe organic phase was separated
4. 4
   Séchagedried over anhydrous sodium sulfate
5. 5
   FiltrationAfter filtration
6. 6
   Concentrationthe filtrate was concentrated in vacuo
7. 7
   AutreThe crude product was purified by column chromatography
8. 8
   Lavageeluted with ethyl acetate/hexanes (20/80 to 30/70)

Mode opératoire

To a solution of 2-benzamido-4-methylthiazole-5-carboxylic acid (0.30 g, 1.14 mmol) in tertahydrofuran (28 mL) was added N-methylmorpholine (0.23 mL, 0.21 g, 2.09 mmol) under nitrogen atmosphere, followed by the addition of isobutyl chloroformate (0.2 mL, 0.21 g, 1.54 mmol) dropwise at ambient temperature. The mixture was stirred at ambient temperature for 7 hours. Benzhydrazide (0.23 g, 1.71 mmol) and 4-methylmorpholine (0.15 mL, 0.14 g, 1.36 mmol) were added to the reaction mixture. After being stirred at ambient temperature for 18 hours, the reaction mixture was diluted with ethyl acetate (50 mL), washed with water (3×10 mL). The organic phase was separated and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated in vacuo. The crude product was purified by column chromatography eluted with ethyl acetate/hexanes (20/80 to 30/70) to afford the title compound as a white solid (0.059 g, 14% yield); m.p. 258-260° C.; 1H NMR (DMSO-d6, 300 MHz) δ 12.90 (br, 1H), 10.46 (s, 1H), 10.10 (s, 1H), 8.09 (d, J=7.4 Hz, 2H), 7.93 (d, J=6.9 Hz, 2H), 7.65-7.47 (m, 6H), 2.56 (s, 3H); MS (ES+) m/z 381.4 (M+1).

Source