반응 #76430

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N-(4-Choro-3-methylisothiazol-5-yl)-[2-(2,2-dimethylpropyl)benzoxazol-5-yl]acetamide

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

N,N-dimethylformamide dimethylacetal

N,N-dimethylformamide

→

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

수율 27.3%

용매

toluene

반응 조건

후처리

1. 1
   온도The mixture as cooled to room temperature
2. 2
   기타the solvent was evaporated in vacuo
3. 3
   세척washed sequentially with brine and water
4. 4
   건조dried over anhydrous magnesium sulfate
5. 5
   여과filtered
6. 6
   기타the filtrate evaporated in vacuo
7. 7
   기타The residue was further purified by flash column chromatography
8. 8
   세척eluting with ethyl acetate
9. 9
   세척Further flash column chromatography, eluting with ethyl acetate

실험 절차

N-(4-Choro-3-methylisothiazol-5-yl)-[2-(2,2-dimethylpropyl)benzoxazol-5-yl]acetamide (2.5 g, 0.0066 mole) [prepared as in Example 1] and N,N-dimethylformamide dimethylacetal (1.5 g, 0.013 mole) were added to a mixture of N,N-dimethylformamide (5 ml) and toluene (20 ml) and the resulting mixture was heated to 110° C. for 4 hours. The mixture as cooled to room temperature and the solvent was evaporated in vacuo. The residue was taken up in ethyl acetate and washed sequentially with brine and water, dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated in vacuo. The residue was further purified by flash column chromatography, eluting with ethyl acetate:hexane at 1:1 by volume. Further flash column chromatography, eluting with ethyl acetate:dichloromethane at 1:9 by volume gave N-(4-chloro-3-methylisothiazol-5-yl)-α-[(dimethylamino)methylene]-[2-(2,2-dimethylpropyl)benzoxazol-5-yl]acetamide (0.78 g) as a single geometrical isomer.

출처