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

HRID 507698노트

반응식

HRID 507698 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-75d55caffc664944a05ae28a9705c613
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786132B2

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