Trimethylsilyl isocyanate → N-hydroxy-N-[6-(3-pyridylmethyl)-2H-1-benzopyran-3-ylmethyl]urea
反応式
C[Si]([N:5]=[C:6]=[O:7])(C)C.[N:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]3[O:23][CH2:22][C:21]([CH2:24][NH:25][OH:26])=[CH:20][C:19]=3[CH:27]=2)[CH:9]=1>O1CCCC1>[OH:26][N:25]([CH2:24][C:21]1[CH2:22][O:23][C:18]2[CH:17]=[CH:16][C:15]([CH2:14][C:10]3[CH:9]=[N:8][CH:13]=[CH:12][CH:11]=3)=[CH:27][C:19]=2[CH:20]=1)[C:6]([NH2:5])=[O:7]参加物
4
実験手順
1.84 ml of trimethylsilyl isocyanate was added dropwise to a solution of 3.03 g (11.3 mmol) of N-[6-(3-pyridylmethyl)-2H-1-benzopyran-3-ylmethyl]hydroxylamine in tetrahydrofuran (30 ml) at 0° C. over 5 minutes, followed by stirring overnight at room temperature. Then, the solvent was evaporated in vacuo, the residue was purified by silica gel chromatography (chloroform:methanol:concentrated ammonia water=300:9:1−100:9:1), followed by recrystallization in a mixed solvent of chloroform-methanol-ethyl acetate to obtain 2.41 g (yield=68.5%) of the desired compound as white columnar crystal.