C(O[Si:4]([O:11][CH2:12][CH3:13])([O:8][CH2:9][CH3:10])[O:5][CH2:6][CH3:7])C.[CH2:14]([NH:16][CH2:17][CH3:18])[CH3:15]>>[CH2:14]([N:16]([Si:4]([O:5][CH2:6][CH3:7])([O:8][CH2:9][CH3:10])[O:11][CH2:12][CH3:13])[CH2:17][CH3:18])[CH3:15]Comparative experiment 6 to The reacted product 13 was performed by direct amino group substitution of tetraethoxy silane not via Grignard reagent. Namely, a 200 mL-volume flask, equipped with an agitating blade and a soxhlet extractor loaded with a monocular shive 4A-stuffed cylindrical paper filter, was employed, of which inside was substituted for nitrogen using a vacuum pump. Then, 83.3 g (0.40 mol) of tetraethoxysilane and 73.1 g (1.0 mol) of diethylamine were fed into the flask, and heated and revolved for 8 hours. Analysis of the resultant reacted solution by gas chromatography confirmed no target amino-substituted product but tetraethoxysilane of the starting substance only.
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