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

HRID 1009185ノート

反応式

HRID 1009185 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-34d2f38f0d8d4bcb9802ac92f3150759
出典データセット
uspto-grants-2011_07
特許番号
US07973062B2

反応ノート

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