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p-Toluenesulfonic acid monohydrate → 7-Bromo-2-tert-butyl-5-methyl-6-styryl-1,3-benzoxazole-4-carbonitrile
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | p-Toluenesulfonic acid monohydrate | HCID 521998 | — |
| 反応物 | Sodium bicarbonate water | HCID 86585896 | — |
| 反応物 | N-(3-Bromo-6-cyano-2-hydroxy-5-methyl-4-styrylphenyl)-2,2-dimethylpropionamide | HCID 86630801 | — |
| 溶媒 | Toluene | HCID 1140 | — |
| 生成物 | 7-Bromo-2-tert-butyl-5-methyl-6-styryl-1,3-benzoxazole-4-carbonitrile | HCID 68584010 | 84.3% |
反応手順
Toluene (3 ml), p-toluenesulfonic acid monohydrate (1.4 mg, 7.5 μmol) were added to N-(3-bromo-6-cyano-2-hydroxy-5-methyl-4-styrylphenyl)-2,2-dimethylpropionamide (I-14) (31 mg, 75 μmol), followed by refluxing with a Dean-Stark condenser for 2.5 hours. After cooling, saturated sodium bicarbonate water (30 ml) was added to the reaction liquid, the product was extracted with ethyl acetate (30 ml×2). The organic layer was washed with saturated brine (30 ml), dried over anhydrous magnesium sulfate, concentrated under reduced pressure, the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=8:1) to obtain the entitled compound (25 mg, 84%) as a colorless solid.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07737166B2 |
| 出典データセット | uspto-grants-2010_06 |
| ORD ID | ord-ff74efec60a34a189d6388ef3f692111 |
| 出典メモ | uspto-grants-2010_06 |