Benzoyl chloride → N-(2-(thiophen-3-yl)ethyl)benzamide

HRID 507698ノート

反応式

HRID 507698 の反応式
Cl.[S:2]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][NH2:9])=[CH:3]1.C(N(CC)CC)C.[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1>[S:2]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][NH:9][C:17](=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:3]1

参加物

5

反応物 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 122587382-(Thiophen-3-yl)ethan-1-amine hydrochloride

生成物 1

HCID 25854160N-(2-(thiophen-3-yl)ethyl)benzamide収率 96.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

2-(Thiophen-3-yl)ethanamine hydrochloride (3 g, 18 mmol) was taken in THF (40 mL) and treated with triethylamine (9.92 mL, 71.2 mmol). The reaction was cooled down to 0° C. and benzoyl chloride (2.55 mL, 21.9 mmol), diluted with THF was added dropwise to the reaction. The reaction was stirred for 3 h and the volatiles removed in vacuo. The residue was dissolved in ethyl acetate and washed with an aqueous saturated solution of sodium bicarbonate, water and brine. The organic solution was dried with sodium sulfate and purified by flash chromatography using a gradient of 25 to 70% ethyl acetate in hexanes to afford an off-white solid (4 g). MS (M+H)+ 232.

後処理

  1. additionwas added dropwise to the reaction
  2. customthe volatiles removed in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with an aqueous saturated solution of sodium bicarbonate, water and brine
  5. dry with materialThe organic solution was dried with sodium sulfate
  6. custompurified by flash chromatography

出典と根拠

ORDレコード
ord-75d55caffc664944a05ae28a9705c613
出典データセット
uspto-grants-2010_08
特許番号
US07786132B2

反応ノート

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