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Stannous Chloride → (Z)-3-(4-aminobenzyl)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dione

HRID 517609
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HRID 517609 반응식
[CH2:1]([O:3][C:4]1[CH:27]=[CH:26][C:7](/[CH:8]=[C:9]2/[C:10](=[O:25])[N:11]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=3)[C:12](=[O:14])[S:13]/2)=[CH:6][CH:5]=1)[CH3:2].[Sn](Cl)Cl>C(Cl)(Cl)Cl.C(O)C.ClCCl>[NH2:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][N:11]2[C:10](=[O:25])/[C:9](=[CH:8]/[C:7]3[CH:26]=[CH:27][C:4]([O:3][CH2:1][CH3:2])=[CH:5][CH:6]=3)/[S:13][C:12]2=[O:14])=[CH:17][CH:18]=1
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참가 물질

5

반응물 2

HCID 24479Stannous ChlorideHCID 1498888(Z)-5-(4-ethoxybenzylidene)-3-(4-nitrobenzyl)thiazolidine-2,4-dione

생성물 1

HCID 71697762(Z)-3-(4-aminobenzyl)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dione

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 21889567Chloroform ethanol용매

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온도
45 °C

실험 절차

To a solution of compound 28n (100 mg, 0.26 mol) in 10 mL of chloroform-ethanol co-solvent (ratio, 4:1) was added tin(II) chloride.dihydrate (293 mg, 1.30 mmol). The reaction mixture was stirred at 45° C. overnight. The reaction mixture was diluted with dichloromethane and washed with sat'd aqueous NaHCO3, collected the organic layer, dried over anhydrous Na2SO4, filtered, concentrated and purified by silica column chromatography (10% ethyl acetate in dichloromethane) to afford 88 mg (97.0%) of pure 28o as a yellow-orange solid.

후처리

  1. washwashed with sat'd aqueous NaHCO3
  2. customcollected the organic layer
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by silica column chromatography (10% ethyl acetate in dichloromethane)

출처 및 근거

ORD 기록
ord-38df7d3e6da349e6860c626c4f6cafc0
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09115122B2

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