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

HRID 860561ノート

反応式

HRID 860561 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]=[C:39]1[NH:43][C:42](=[O:44])[CH2:41][S:40]1>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:43]2[C:42](=[O:44])[C:41](=[CH2:1])[S:40][C:39]2=[S:38])[CH:30]=[CH:29]3)[CH:21]=[CH:22][C:23]=1[O:24][CH3:25])([CH3:17])([CH3:15])[CH3:16]

参加物

6

反応物 4

HCID 1140TolueneHCID 8082PiperidineHCID 1201546RhodanineHCID 865860436-[3-(t-Butyl)-4-methoxyphenyl]-2-naphthaldehyde

生成物 1

HCID 865860446-[3-(t-Butyl)-4-methoxyphenyl]-naphthalen-2-yl-methylene-2-thioxo-4-thiazolidinone収率 56%

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 (0.100 g, 0.31 mmol) and 2-thioxo-4-thiazolidinone (0.041 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 washed with EtOH and H2O. The solid was dried under high vacuum to afford 0.076 g (56%) of 6-[3-(t-butyl)-4-methoxyphenyl]-naphthalen-2-yl-methylene-2-thioxo-4-thiazolidinone, mp 281–284° C. 1H NMR (300 MHz, DMSO-d6): δ 1.40 (s, 9H), 3.86 (s, 3H), 7.11 (d, J=8.4 Hz, 1H), 7.61–7.70 (m, 3H), 7.77 (s, 1H), 7.89 (d, J=8.4 Hz, 1H), 8.09 (dd, J1=8.4 Hz, J2=3.0 Hz, 2H), 8.10 (s, 2H), 13.9 (brs, 1H).

後処理

  1. temperatureat reflux for 16.5 hours under an argon atmosphere
  2. filtrationThe resulting suspension was filtered
  3. washthe solid was washed with EtOH and H2O
  4. customThe solid was dried under high vacuum

出典と根拠

ORDレコード
ord-ff2e6de02c814dfe901a58c9ba7b41af
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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