Toluene → 6-[3-(1-Adamantyl)-4-methoxyphenyl]-naphthalen-2-yl-methylene-2,4-thiazolidinedione

HRID 860543ノート

反応式

HRID 860543 の反応式
[C:1]1(C)C=CC=CC=1.N1CCCCC1.[C:14]12([C:24]3[CH:25]=[C:26]([C:32]4[CH:33]=[C:34]5[C:39](=[CH:40][CH:41]=4)[CH:38]=[C:37](C=O)[CH:36]=[CH:35]5)[CH:27]=[CH:28][C:29]=3[O:30][CH3:31])[CH2:23][CH:18]3[CH2:19][CH:20]([CH2:22][CH:16]([CH2:17]3)[CH2:15]1)[CH2:21]2.[S:44]1[CH2:48][C:47](=[O:49])[NH:46][C:45]1=[O:50]>C(O)(=O)C>[C:14]12([C:24]3[CH:25]=[C:26]([C:32]4[CH:33]=[C:34]5[C:39](=[CH:40][CH:41]=4)[CH:38]=[C:37]([N:46]4[C:47](=[O:49])[C:48](=[CH2:1])[S:44][C:45]4=[O:50])[CH:36]=[CH:35]5)[CH:27]=[CH:28][C:29]=3[O:30][CH3:31])[CH2:23][CH:18]3[CH2:19][CH:20]([CH2:22][CH:16]([CH2:17]3)[CH2:15]1)[CH2:21]2

参加物

6

反応物 4

HCID 1140TolueneHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 865860366-[3-(1-Adamantyl)-4-methoxyphenyl]-2-naphthaldehyde

生成物 1

HCID 865860356-[3-(1-Adamantyl)-4-methoxyphenyl]-naphthalen-2-yl-methylene-2,4-thiazolidinedione収率 71%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A solution of toluene (150 mL), piperidine (0.48 mL), acetic acid (0.51 mL), 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthaldehyde (5.84 g, 14.75 mmol) and 2,4-thiazolidinedione (1.73 g, 14.75 mmol) was heated at reflux for 18 hours under an argon atmosphere. The resulting suspension was filtered and the solid was stirred at room temperature in 30 mL of EtOH. After 30 minutes the solid was filtered and dried under high vacuum to afford 5.3 g (71%) of 6-[3-(1-adamantyl)-4-methoxyphenyl]-naphthalen-2-yl-methylene-2,4-thiazolidinedione, mp 286–287° C. 1H NMR (300 MHz; DMSO-d6): 1.76 (brs, 6H), 2.07–2.14 (m, 9H), 3.87 (s, 3H), 7.11 (d, J=8.4 Hz, 1H), 7.58 (s, 1H), 7.66 (t, J=9.3 Hz, 2H), 7.88–7.93 (m, 2H), 8.09 (t, J=8.7 Hz, 2H), 8.18 (d, J=5.7 Hz, 2H), 12.63 (brs, 1H).

後処理

  1. temperatureat reflux for 18 hours under an argon atmosphere
  2. filtrationThe resulting suspension was filtered
  3. filtrationAfter 30 minutes the solid was filtered
  4. customdried under high vacuum

出典と根拠

ORDレコード
ord-eb188f8f51524e299b203239e75c454e
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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