関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Sodium Hydroxide | HCID 14798 | — |
| 反応物 | 2,4-Dichloropyrimidine | HCID 77531 | — |
| 反応物 | Sodium borohydride | HCID 4311764 | — |
| 反応物 | Sodium hydrosulfide hydrate | HCID 16211346 | — |
| 反応物 | 3-Chloro-2-methyl-4-thiocyanatoaniline | HCID 37859309 | — |
| 溶媒 | Methanol--water (1/1) | HCID 22242641 | — |
| 生成物 | 3-Chloro-4-[(2-chloropyrimidin-4-yl)thio]-2-methylaniline | HCID 59491674 | 51.4% |
反応手順
Crude 4-amino-2-chloro-3-methylphenyl thiocyanate (600 mg, 3.0 mmol) was dissolved in a mixture of methanol:water (2:1, 22 mL) and cooled to 0° C. Sodium hydrosulfide monohydrate (338 mg, 4.6 mmol) and sodium borohydride (447 mg, 11.8 mmol) were added then the mixture was allowed to warm to room temperature and stir overnight. After this time sodium hydroxide (96 mg, 2.4 mmol) was added followed by 2,4-dichloropyrimidine (360 mg, 2.4 mmol) and the mixture allowed to stir for a further 24 h. The methanol was removed in vacuo and then the mixture was extracted with ethyl acetate. The extracts were dried (Na2SO4) and evaporated then the residue was purified by flash chromatography to afford 3-chloro-4-[(2-chloropyrimidin-4-yl)thio]-2-methylaniline (353 mg, 41%).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 特許番号 | US08846704B2 |
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| 出典データセット | uspto-grants-2014_09 |
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| ORD ID | ord-4ade47deac6c4594a6d8c90bd28d38c0 |
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| 出典メモ | uspto-grants-2014_09 |
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