Benzoic Acid → 5-(3,4-Bis-methoxymethoxy-benzylidene)-thiazolidine-2,4-dione

HRID 1866453ノート

反応式

HRID 1866453 の反応式
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][O:15][CH3:16])[CH:8]=O.[S:17]1[CH2:21][C:20](=[O:22])[NH:19][C:18]1=[O:23].C(O)(=O)C1C=CC=CC=1.N1CCCCC1>C1(C)C=CC=CC=1.CCCCCC>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][O:15][CH3:16])[CH:8]=[C:21]1[S:17][C:18](=[O:23])[NH:19][C:20]1=[O:22]

参加物

7

反応物 4

HCID 243Benzoic AcidHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 117463143,4-Bis(methoxymethoxy)benzaldehyde

生成物 1

HCID 766944395-(3,4-Bis-methoxymethoxy-benzylidene)-thiazolidine-2,4-dione

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8058Hexane溶媒

実験手順

A mixture of 3,4-Bis-methoxymethoxy-benzaldehyde (5 mmol), thiazolidine-2,4-dione (5 mmol), benzoic acid (0.5 mmol), and piperidine (0.5 mmol) in toluene (150 mL) was heated to reflux for 15 h. Upon cooling, to the reaction mixture was added hexane (50 mL). The resulting suspension was gently stirred for 2 min and then allowed to settle. It was then filtrated and the solid was washed with cold benzene. 5-(3,4-Bis-methoxymethoxy-benzylidene)-thiazolidine-2,4-dione was obtained as a yellow solid (yield 92%). 1H-NMR (300 MHz, CDCl3) δ (ppm) 7.81 (s, 1H), 7.38 (d, J=2.0 Hz, 1H), 7.28-7.25(m, 1H), 7.18-7.15 (m, 1H), 5.32 (s, 2H), 5.63 (s, 2H), 3.57 (s, 3H), 3.54 (s, 3H). 13C-NMR (75 MHz) δ (ppm) 168.1, 167.6, 149.8, 147.9, 134.6, 127.7, 126.1, 121.0, 118.8, 116.8, 96.0, 95.5, 56.9, 56.8.

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 15 h
  3. temperatureUpon cooling, to the reaction mixture
  4. filtrationIt was then filtrated
  5. washthe solid was washed with cold benzene

出典と根拠

ORDレコード
ord-5c104b480499404bb286f5bdbf04c23c
出典データセット
uspto-grants-2009_12
特許番号
US07629375B2

反応ノート

読み込み中…