Acetic Anhydride → (Z)-N-(2-(5-(4-ethoxybenzylidene)-2,4-dioxothiazolidin-3-yl)ethyl)acetamide

HRID 517589노트

반응식

HRID 517589 반응식
[NH2:1][CH2:2][CH2:3][N:4]1[C:8](=[O:9])/[C:7](=[CH:10]/[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH3:19])=[CH:13][CH:12]=2)/[S:6][C:5]1=[O:20].C(N(CC)CC)C.[C:28](OC(=O)C)(=[O:30])[CH3:29]>ClCCl>[CH2:18]([O:17][C:14]1[CH:15]=[CH:16][C:11](/[CH:10]=[C:7]2/[C:8](=[O:9])[N:4]([CH2:3][CH2:2][NH:1][C:28](=[O:30])[CH3:29])[C:5](=[O:20])[S:6]/2)=[CH:12][CH:13]=1)[CH3:19]

참가 물질

5

반응물 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 1249836(Z)-3-(2-aminoethyl)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dione

생성물 1

HCID 45485995(Z)-N-(2-(5-(4-ethoxybenzylidene)-2,4-dioxothiazolidin-3-yl)ethyl)acetamide수율 88.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of compound 76 (101 mg, 0.25 mmol) in 5 mL of dichloromethane was added triethylamine (105 μL, 0.75 mmol) and acetic anhydride (26.0 μL, 0.28 mmol). After being stirred at room temperature overnight, the reaction solution was diluted with 50 mL of dichloromethane, washed with water, collected the organic layer, dried over Na2SO4, filtered, concentrated and purified by silica column chromatography (33% dichloromethane in ethyl acetate) to afford 74 mg (88.6%) of the title compound 25a as a light-yellow solid.

후처리

  1. washwashed with water
  2. customcollected the organic layer
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by silica column chromatography (33% dichloromethane in ethyl acetate)

출처 및 근거

ORD 기록
ord-09a94cdb5ea44a67a36ffaf1f42536b7
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115122B2

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