Thiazolidinedione → 5-[3-(1-Methyl-cyclohexylmethoxy)-benzylidene]-thiazolidine-2,4-dione

HRID 1009185노트

반응식

HRID 1009185 반응식
[CH3:1][C:2]1([CH2:8][O:9][C:10]2[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=2)[CH:13]=O)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[S:18]1[CH2:22][C:21](=[O:23])[NH:20][C:19]1=[O:24].N1CCCCC1>CCO>[CH3:1][C:2]1([CH2:8][O:9][C:10]2[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=2)[CH:13]=[C:22]2[S:18][C:19](=[O:24])[NH:20][C:21]2=[O:23])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

참가 물질

5

반응물 3

HCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 248277673-(1-Methyl-cyclohexylmethoxy)-benzaldehyde

생성물 1

HCID 743268405-[3-(1-Methyl-cyclohexylmethoxy)-benzylidene]-thiazolidine-2,4-dione수율 67%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture consisting of compound v (0.5 mmol), 2,4-thiazolidinedione (0.6 mmol) and catalytic amounts of piperidine was refluxed in EtOH (5 mL) for 24 h and then concentrated. The oily product was dissolved in ethyl acetate, poured into water and acidified with AcOH. The solution was extracted with ethyl acetate, dried and concentrated. The residue was purified by silica gel chromatography, providing compound 1 in 67% yield. 1H NMR (300 MHz, CDCl3) δ 1.04 (s, 3H), 1.46-1.56 (m, 10H), 3.69 (s, 2H), 6.78-7.28 (m, 2H), 7.08 (d, J=8.40 Hz, 1H), 7.39 (dt, J=2.10, 8.40 Hz, 1H), 7.84 (s, 1H), 8.21-8.78 (br, 1H); HRMS exact mass of (M+Na)+, 354.1140 amu; observed mass of (M+Na)+, 354.113 amu.

후처리

  1. concentrationconcentrated
  2. dissolutionThe oily product was dissolved in ethyl acetate
  3. additionpoured into water
  4. extractionThe solution was extracted with ethyl acetate
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-34d2f38f0d8d4bcb9802ac92f3150759
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07973062B2

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