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

HRID 1157985노트

반응식

HRID 1157985 반응식
[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].N1CCCCC1.CO>C(O)(=O)C.O>[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

참가 물질

7

반응물 4

HCID 1264-Hydroxybenzaldehyde2회HCID 887MethanolHCID 5437Thiazolidinedione2회HCID 8082Piperidine

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매

실험 절차

A mixture of 4-hydroxy benzaldehyde, 36 (3 g, 24.6 mmol), 2,4-thiazolidinedione, 37 (2.9 g, 24.8 mmol), piperidine (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 38, 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).

후처리

  1. temperaturewas refluxed for 18 h

출처 및 근거

ORD 기록
ord-86bd44a3b7fc4e1399930d3d4ee1ebad
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07807712B2

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