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Potassium Iodide → 2-[(2-amino-1,3-thiazol-4-yl)methoxy]-1H-isoindole-1,3(2H)-dione
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Potassium Iodide | HCID 4875 | — |
| 反応物 | N-Hydroxyphthalimide | HCID 10665 | — |
| 反応物 | Cesium carbonate | HCID 10796 | — |
| 反応物 | 2-Thiazolamine, 4-(chloromethyl)-, hydrochloride (1:1) | HCID 73228 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Acetonitrile | HCID 6342 | — |
| 生成物 | 2-[(2-amino-1,3-thiazol-4-yl)methoxy]-1H-isoindole-1,3(2H)-dione | HCID 341077 | 43% |
反応手順
To a solution of 2-hydroxy-1H-isoindole-1,3(2H)-dione (4.13 g, 15.0 mmol) in acetonitrile (150 mL) were added 4-(chloromethyl)-1,3-thiazol-2-amine hydrochloride (50.1 g, 337 mmol), cesium carbonate (210 g, 643 mmol) and potassium iodide (2.54 g, 15.3 mmol). The heterogenous mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with water, the insolubles were filtered off, rinsed with water and dried over night to afford 2-[(2-amino-1,3-thiazol-4-yl)methoxy]-1H-isoindole-1,3(2H)-dione as a colourless solid [36.0 g, yield 43%; HPLC/MS: m/z=276 (M+H); log P(HCOOH)=0.74].
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08580799B2 |
| 出典データセット | uspto-grants-2013_11 |
| ORD ID | ord-e2ea30608b7442e6bab564d433391754 |
| 出典メモ | uspto-grants-2013_11 |