反応式
[S:1]1[C:9]2[CH:8]=[CH:7][NH:6][C:5](=[O:10])[C:4]=2[CH:3]=[CH:2]1.C([N-:14]C(C)C)(C)C.[Li+].O.O.O.C([O-])(=O)C.[Na+].N[O:28][S:29]([OH:32])(=O)=O>O1CCCC1>[S:29]([C:2]1[S:1][C:9]2[CH:8]=[CH:7][NH:6][C:5](=[O:10])[C:4]=2[CH:3]=1)(=[O:32])(=[O:28])[NH2:14]参加物
反応条件
- 温度
- -70 °C
実験手順
To a suspension of thieno[3,2-c]pyridin-4(5H)-one (1.51 g, 10 mmol) in distilled tetrahydrofuran (20 ml), cooled to -70° C. and under a nitrogen atmosphere, was added dropwise 0.7 M lithium diisopropylamide in THF (36 ml, 25 mmol). After one hour, sulfur dioxide gas was bubbled over the surface of this suspension and the reaction was allowed to gradually warm to room temperature. The mixture was diluted with diethyl ether and the precipitated lithium sulfinate intermediate was collected (3.6 g). This salt was dissolved in water (25 ml) and sodium acetate trihydrate (5.4 g, 66 mmol) and hydroxylamine-O-sulfonic acid (2.5 g, 22 mmol) were added. After stirring for 16 hours, the precipitated product was collected by filtration. The product was purified by recrystallization from hot dimethyl sulfoxide by dilution with ethanol to give 1.35 g (59% yield); m.p. 300°-301° C.
後処理
- customsulfur dioxide gas was bubbled over the surface of this suspension
- temperatureto gradually warm to room temperature
- additionThe mixture was diluted with diethyl ether
- customthe precipitated lithium sulfinate intermediate was collected (3.6 g)
- dissolutionThis salt was dissolved in water (25 ml)
- filtrationthe precipitated product was collected by filtration
- customThe product was purified by recrystallization from hot dimethyl sulfoxide by dilution with ethanol
- customto give 1.35 g (59% yield)
出典と根拠
- ORDレコード
- ord-a274d51fe65e4447ac79e6f2d07b6955
- 出典データセット
- uspto-grants-1988_03
- 特許番号
- US04731368
関連ノート
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