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Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → Methyl (3-chloro-4-(6-methyl-2-benzothiazolyl)aminophenyl)acetate
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) | HCID 466102 | — |
| 反応物 | 2-bromo-6-methylbenzo[d]thiazole | HCID 11708414 | — |
| 反応物 | Methyl 2-(4-amino-3-chlorophenyl)acetate | HCID 13616273 | — |
| 溶媒 | O-Xylene | HCID 7237 | — |
| 生成物 | Methyl (3-chloro-4-(6-methyl-2-benzothiazolyl)aminophenyl)acetate | HCID 58778443 | 26% |
反応手順
In xylene (10 ml), 2-bromo-6-methylbenzothiazole (703 mg, 3.08 mmol), methyl 4-amino-3-chlorophenylacetate (615 mg, 3.08 mmol), and pyridinium p-toluenesulfonate (PPTS) (232 mg, 0.92 mmol) were heated under reflux for 10 hours. After cooling, the reaction mixture was distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from n-hexane/ethyl acetate (6:1, v/v) eluate fractions, methyl (3-chloro-4-(6-methyl-2-benzothiazolyl)aminophenyl)acetate (274 mg, 26%) was obtained as a pale yellow solid.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07157487B2 |
| 出典データセット | uspto-grants-2007_01 |
| ORD ID | ord-5ed36a50cb3947d499c75b1a568ec65e |
| 出典メモ | uspto-grants-2007_01 |