化工社化工社 化学情報印刷レポート · 研究参考用
Triethylamine hydrochloride → 3-Methyl-5-(4-nitrophenoxymethyl)-1,2,4-oxadiazole
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Triethylamine hydrochloride | HCID 11130 | — |
| 反応物 | (4-Nitrophenoxy)acetic acid | HCID 15720 | — |
| 反応物 | Diisopropylethylamine | HCID 81531 | — |
| 反応物 | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | 3-Methyl-5-(4-nitrophenoxymethyl)-1,2,4-oxadiazole | HCID 22060445 | 60.4% |
反応手順
A mixture of 4-nitrophenoxy acetic acid (2.25 g, 11.4 mmole), acetamideoxime, triethylamine hydrochloride (3.85 g, 27.62 mmole), EDCI.HCl (4.37 g, 22.79 mmole) and diisopropylethylamine (7.42 g, 57.40 mmole) in anhydrous THF (250 ml) was refluxed for 18 h. The unhomogenous brown colored reaction mixture was quenched with water and extracted with EtOAc (3×300 mL). The combined organic layers washed successively with aqueous NaHCO3, brine and dried over anhydrous Na2SO4. Removal of solvent and purified by chromatographic purification provided 5-[(4-nitrophenoxy)methyl]-3-methyl-1,2,4-oxadiazole (1.62 g, 60%). 1H NMR (CDCl3): δ 8.24 (d, 2H, J=8.8 Hz), 7.08 (d, 2H, J=8.8 Hz), 5.36 (s, 2H), 2.44 (s, 3H).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US09346765B2 |
| 出典データセット | uspto-grants-2016_05 |
| ORD ID | ord-7c66173fc4ac49869007d083a01e8ca7 |
| 出典メモ | uspto-grants-2016_05 |