반응 #76431

반응 방정식

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

수율 85.4%

용매

tetrahydrofuran

water

반응 조건

후처리

1. 1
   온도The mixture was cooled to room temperature
2. 2
   기타the solvent was evaporated in vacuo
3. 3
   기타the residue partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
4. 4
   추출The organic extract
5. 5
   건조was dried over anhydrous magnesium sulfate
6. 6
   여과filtered
7. 7
   기타the filtrate was evaporated in vacuo
8. 8
   기타Further purification by flash column chromatography
9. 9
   세척eluting with ethyl acetate

실험 절차

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.

출처