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Triethylamine → 4-Amino-3-chloro-N,N-dimethylbenzamide
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Triethylamine | HCID 8471 | — |
| 反応物 | Dimethylamine, hydrochloride | HCID 10473 | — |
| 反応物 | 4-Amino-3-chlorobenzoic acid | HCID 17211 | — |
| 反応物 | 1-Hydroxybenzotriazole | HCID 75771 | — |
| 反応物 | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| 溶媒 | Isopropanol | HCID 3776 | — |
| 溶媒 | Chloroform | HCID 6212 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 生成物 | 4-Amino-3-chloro-N,N-dimethylbenzamide | HCID 20287481 | 59.6% |
反応手順
To a solution of 4-amino-3-chlorobenzoic acid (1 equiv) in DCM (0.12 M) was added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (1.2 equiv), 1-hydroxybenzotriazole (1.2 equiv), triethylamine (4 equiv) and dimethylamine hydrochloride (2 equiv) sequentially. The mixture was stirred at room temperature overnight. After the reaction was complete, as monitored by LCMS, the mixture was diluted with a mixture of isopropanol in chloroform (30%), washed with water and dried over anhydrous sodium sulfate. The organic phase was concentrated and the residue obtained was recrystallized in the mixture of hexane and ethyl acetate (10%) to afford the desired product (Yield: 59.6%) as a light brown solid. MS (ESI) m/z 199.1 [M+1]+.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US09428509B2 |
| 出典データセット | uspto-grants-2016_08 |
| ORD ID | ord-d061683f71294405bc82d662ae7fa1c6 |
| 出典メモ | uspto-grants-2016_08 |