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Triethylamine → N-methoxy-N,1-dimethyl-1H-benzo[d]imidazole-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-Methyl-1H-benzimidazole-5-carboxylic acid | HCID 4913063 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 生成物 | N-methoxy-N,1-dimethyl-1H-benzo[d]imidazole-5-carboxamide | HCID 86665700 | 80% |
反応手順
A suspension of 1-methyl-1H-benzo[d]imidazole-5-carboxylic acid (9.7 g, 1.0 eq), EDCI (10.5 g, 1.2 eq), and HOBt (7.4 g, 1.2 eq) in 150 mL CH2Cl2 was stirred at rt for 5 min, and then N-methoxymethanamine hydrochloride (6.7 g, 1.5 eq) and Et3N (18.5 g, 4.0 eq) were added. The reaction mixture was stirred at rt overnight. Water was added and extracted with CH2Cl2. The extract was dried, concentrated, and purified by column chromatography to give the desired product (9.5 g, 80%). 1H NMR (400 MHz, CDCl3) δ 8.20 (d, J=1.2 Hz, 1H), 7.93 (s, 1H), 7.72 (dd, J=8.8 Hz, 1.6 Hz, 1H), 7.40 (dd, J=8.4 Hz, 0.8 Hz, 1H), 3.87 (s, 3H), 3.57 (s, 3H), 3.40 (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-8cdf096c8eec4819ac754e6c42a6c534 |
| 出典メモ | uspto-grants-2016_04 |