Reaktion #76431

Reaktionsgleichung

N-(4-chloro-3-methylisothiazol-5-yl)-α-[(dimethylamino)methylene]-[2-(2,2-dimethylpropyl)benzoxazol-5-yl]acetamide

ethylamine hydrochloride

→

N-(4-chloro-3-methylisothiazol-5-yl)-α-[(ethylamino)methylene]-[2-(2,2-dimeth-ylpropyl)benzoxazol-5-yl]acetamide

Ausbeute 85.4%

Lösungsmittel

tetrahydrofuran

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was cooled to room temperature
2. 2
   Sonstigethe solvent was evaporated in vacuo
3. 3
   Sonstigethe residue partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
4. 4
   ExtraktionThe organic extract
5. 5
   Trocknenwas dried over anhydrous magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Sonstigethe filtrate was evaporated in vacuo
8. 8
   SonstigeFurther purification by flash column chromatography
9. 9
   Wascheneluting with ethyl acetate

Vorschrift

A mixture of N-(4-chloro-3-methylisothiazol-5-yl)-α-[(dimethylamino)methylene]-[2-(2,2-dimethylpropyl)benzoxazol-5-yl]acetamide (0.20 g, 0.00046 mole) [from Example 5] and ethylamine hydrochloride (0.0225 g, 0.0028 mole) in tetrahydrofuran (4 ml) and water (1 ml) was heated for 24 hours at 60° C. The mixture was cooled to room temperature, the solvent was evaporated in vacuo and the residue partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The organic extract was dried over anhydrous magnesium sulfate, filtered and the filtrate was evaporated in vacuo. Further purification by flash column chromatography, eluting with ethyl acetate:hexane at 2:3 by volume, gave N-(4-chloro-3-methylisothiazol-5-yl)-α-[(ethylamino)methylene]-[2-(2,2-dimeth-ylpropyl)benzoxazol-5-yl]acetamide as a colourless solid (0.17 g). Analysis by 1H NMR showed the product comprised a mixture of E- and Z-isomers.

Quelle