Toluene → 6-[3-(t-Butyl)-4-methoxyphenyl]-naphthalen-2-yl-methylene-2,4-thiazolidinedione

HRID 860556ノート

反応式

HRID 860556 の反応式
[C:1]1(C)C=CC=CC=1.N1CCCCC1.[C:14]([C:18]1[CH:19]=[C:20]([C:26]2[CH:27]=[C:28]3[C:33](=[CH:34][CH:35]=2)[CH:32]=[C:31](C=O)[CH:30]=[CH:29]3)[CH:21]=[CH:22][C:23]=1[O:24][CH3:25])([CH3:17])([CH3:16])[CH3:15].[S:38]1[CH2:42][C:41](=[O:43])[NH:40][C:39]1=[O:44]>C(O)(=O)C>[C:14]([C:18]1[CH:19]=[C:20]([C:26]2[CH:27]=[C:28]3[C:33](=[CH:34][CH:35]=2)[CH:32]=[C:31]([N:40]2[C:41](=[O:43])[C:42](=[CH2:1])[S:38][C:39]2=[O:44])[CH:30]=[CH:29]3)[CH:21]=[CH:22][C:23]=1[O:24][CH3:25])([CH3:15])([CH3:17])[CH3:16]

参加物

6

反応物 4

HCID 1140TolueneHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 865860436-[3-(t-Butyl)-4-methoxyphenyl]-2-naphthaldehyde

生成物 1

HCID 865860426-[3-(t-Butyl)-4-methoxyphenyl]-naphthalen-2-yl-methylene-2,4-thiazolidinedione収率 28%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A solution of toluene (2.5 mL), piperidine (0.003 mL), acetic acid (0.003 mL), 6-[3-(t-butyl)-4-methoxyphenyl]-2-naphthaldehyde (0.124 g, 0.31 mmol) and 2,4-thiazolidinedione (0.036 mg, 0.31 mmol) was heated at reflux for 16.5 hours under an argon atmosphere. The resulting suspension was filtered and the solid was stirred at room temperature in EtOH. After 3 hours, the solid was filtered and dried under high vacuum to afford 0.037 g (28%) of 6-[3-(t-butyl)-4-methoxyphenyl]-naphthalen-2-yl-methylene-2,4-thiazolidinedione, mp 274–276° C. 1H NMR (300 MHz, DMSO-d6): δ 1.40 (s, 9H), 3.86 (s, 3H), 7.11 (d, J=8.4 Hz, 1H), 7.63 (s, 1H), 7.66 (t, J=8.1 Hz, 2H), 7.88 (d, J=8.4 Hz, 1H), 7.92 (s, 1H), 8.07 (d, J=8.4 Hz, 1H), 8.08 (d, J=8.4 Hz, 1H), 8.17 (brs, 2H), 12.60 (brs, 1H).

後処理

  1. temperatureat reflux for 16.5 hours under an argon atmosphere
  2. filtrationThe resulting suspension was filtered
  3. filtrationthe solid was filtered
  4. customdried under high vacuum

出典と根拠

ORDレコード
ord-245b17a7f23f4ecc8a67d40c045f6145
出典データセット
uspto-grants-2006_12
特許番号
US07153875B2

反応ノート

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