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Mesitylene → 3-[Acetyl-(3,5-dichlorophenyl)-amino]-4-methoxybenzoic acid methyl ester
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Mesitylene | HCID 7947 | — |
| 反応物 | Ethyl Acetate | HCID 8857 | — |
| 反応物 | Benzene, 1-bromo-3,5-dichloro- | HCID 29766 | — |
| 反応物 | Sodium Bicarbonate | HCID 516892 | — |
| 反応物 | Methyl 2-acetamido-4-methoxybenzoate | HCID 54415798 | — |
| 触媒 | Copper iodide | HCID 83717 | — |
| 生成物 | 3-[Acetyl-(3,5-dichlorophenyl)-amino]-4-methoxybenzoic acid methyl ester | HCID 54300158 | — |
反応手順
A mixture of 2-acetylamino-4-methoxybenzoic acid methyl ester (9.58 g, 42.92 mmol), 1-bromo-3,5-dichlorobenzene (28.80 g, 127.48 mmol), copper iodide (2.32 g, 12.18 mmol), and sodium bicarbonate (8.72 g, 103.80 mmol) in of mesitylene (60 mL) was heated to reflux. After 7 days, the mixture was allowed to cool and was diluted with ethyl acetate (300 mL). The resulting solid was removed by filtration and washed with ethyl acetate. The filtrate was concentrated in vacuo and the residue was chromatographed on silica gel eluting with hexane/ethyl acetate (9:1→1:1) to afford the product (11.6 g); m.p. 100-101° C. after trituration in hexane.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US06268387B1 |
| 出典データセット | uspto-grants-2001_07 |
| ORD ID | ord-756f52fcbc6e470d8dd0e668fcf7c965 |
| 出典メモ | uspto-grants-2001_07 |