4-Hydroxybenzaldehyde → (5E)-5-[(4-Hydroxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione

HRID 1868607ノート

反応式

HRID 1868607 の反応式
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[S:10]1[CH2:14][C:13](=[O:15])[NH:12][C:11]1=[O:16].CO.O>C(O)(=O)C>[CH:4]1[C:5](/[CH:6]=[C:14]2\[C:13]([NH:12][C:11]([S:10]\2)=[O:16])=[O:15])=[CH:8][CH:9]=[C:2]([OH:1])[CH:3]=1

参加物

6

反応物 4

HCID 1264-Hydroxybenzaldehyde2 回HCID 887MethanolHCID 962WaterHCID 5437Thiazolidinedione2 回

生成物 1

HCID 1276528(5E)-5-[(4-Hydroxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A mixture of 4-hydroxy benzaldehyde, 53 (3 g, 24.6 mmol), 2,4-thiazolidinedione, 54 (2.9 g, 24.8 mmol), pipieridine (2.5 mL) and methanol (100 mL) was refluxed for 18 h. The reaction mixture was poured into water and acidified with acetic acid to give 55, which was recrystallised from methanol. Yield 4.7 g (86%); mp 296-298° C.; MS (FAB) 222 (M++1); IR (KBr) 3404, 3123, 1723, 1678; 1H NMR (200 MHz, DMSO-d6) δ 7.70 (s, 1H), 7.46 (d, J=8.6 Hz, 2H), 6.93 (d, J=8.6 Hz, 2H).

後処理

  1. temperaturewas refluxed for 18 h

出典と根拠

ORDレコード
ord-da40fd71646040c4a9bd77f2cba17a0c
出典データセット
uspto-grants-2009_12
特許番号
US07635779B2

反応ノート

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