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

HRID 860543노트

반응식

HRID 860543 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-eb188f8f51524e299b203239e75c454e
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07153875B2

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