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Benzoic Acid → 5-[4-(4'-Methoxybiphenyl-3-yloxy)-benzylidene]-thiazolidine-2,4-dione

HRID 2217638
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인쇄 미리보기

반응식

HRID 2217638 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:16]3[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=3)[CH:10]=2)=[CH:5][CH:4]=1.[S:24]1[CH2:28][C:27](=[O:29])[NH:26][C:25]1=[O:30].C(O)(=O)C1C=CC=CC=1.N1CCCCC1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:16]3[CH:23]=[CH:22][C:19]([CH:20]=[C:28]4[S:24][C:25](=[O:30])[NH:26][C:27]4=[O:29])=[CH:18][CH:17]=3)[CH:10]=2)=[CH:7][CH:8]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 243Benzoic AcidHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 593029604-(4'-Methoxybiphenyl-3-yloxy)-benzaldehyde

생성물 1

HCID 853403575-[4-(4'-Methoxybiphenyl-3-yloxy)-benzylidene]-thiazolidine-2,4-dione수율 77.5%

시약·촉매·용매 1

HCID 1140
Toluene
용매

실험 절차

A mixture of 57 (1.23 g, 4.0 mmol), 2,4-thiazolidinedione (0.48 g, 4.0 mmol), benzoic acid (0.60 g, 4.8 mmol) and piperidine (0.61 mL, 6.0 mmol) in toluene (30 mL) was heated to a vigorous reflux until most of the solvent had evaporated. A yellow suspension was achieved by addition of acetic acid (25 mL) followed by sonication. Filtration of the suspension followed by washing with acetic acid (10 mL) yielded 58 (1.25 g, 75%) after filtration and oven drying. 1H NMR (400 MHz, DMSO-d6): δ 12.57 (br s, 1H), 7.78 (s, 1H), 7.63 (d, J=8.8 Hz, 2H), 7.62 (d, J=8.8 Hz, 2H), 7.49 (d, J=5.2 Hz, 2H), 7.36 (t, J=1.6 Hz, 1H), 7.16 (d, J=8.8 Hz, 2H), 7.03 (m, 1H), 7.01 (d, J=8.8 Hz, 2H), 3.7 (s, 3H).

후처리

  1. temperaturewas heated to
  2. temperaturea vigorous reflux until most of the solvent
  3. customhad evaporated
  4. additionA yellow suspension was achieved by addition of acetic acid (25 mL)
  5. customfollowed by sonication
  6. filtrationFiltration of the suspension
  7. washby washing with acetic acid (10 mL)

출처 및 근거

ORD 기록
ord-166605d53bd54cb3a60b8af865b3aa6b
출처 데이터셋
uspto-grants-2008_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07407978B2

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