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Triethylamine → N-methoxy-N-methylbenzo[d]oxazole-5-carboxamide
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Triethylamine | HCID 8471 | — |
| 反応物 | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| 反応物 | 1-Hydroxybenzotriazole | HCID 75771 | — |
| 反応物 | Methanamine, N-methoxy-, hydrochloride (1:1) | HCID 81138 | — |
| 反応物 | 1,3-Benzoxazole-5-carboxylic acid | HCID 19006767 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 生成物 | N-methoxy-N-methylbenzo[d]oxazole-5-carboxamide | HCID 89672883 | 60.9% |
反応手順
To a solution of benzo[d]oxazole-5-carboxylic acid (7.8 g, 1.0 eq), N,O-dimethylhydroxylamine hydrochloride (7.0 g, 1.5 eq), HOBt (7.76 g, 1.2 eq) and EDCI (11 g, 1.2 eq) in 100 mL CH2Cl2 was added Et3N (19 g, 4.0 eq) dropwise at 0° C. The mixture was then stirred at rt overnight, concentrated, and purified by column chromatography with petroleum ether:EtOAc=1:1 to give the desired product (6.0 g, 51%). 1H NMR (400 MHz, CDCl3) δ 8.18 (s, 1H), 8.16 (1H), 7.80 (d, J=8.4 Hz, 1H), 7.62 (d, J=8.0 Hz, 1H), 3.56 (s, 3H), 3.41 (s, 3H).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US09309211B2 |
| 出典データセット | uspto-grants-2016_04 |
| ORD ID | ord-5e137fd6d0c74ac4847606494e9d4ee1 |
| 出典メモ | uspto-grants-2016_04 |