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Benzoic Acid → 2-{4-[4-(2,4-Dioxothiazolidin-5-ylidenemethyl)-phenoxy]-phenyl}-3-p-tolylacrylic acid

HRID 2238257
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HRID 2238257 반응식
[CH:1]([C:3]1[CH:27]=[CH:26][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([C:14](=[CH:18][C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)[C:15]([OH:17])=[O:16])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1)=O.[S:28]1[CH2:32][C:31](=[O:33])[NH:30][C:29]1=[O:34].C(O)(=O)C1C=CC=CC=1.N1CCCCC1.Cl>C1(C)C=CC=CC=1>[O:34]=[C:29]1[NH:30][C:31](=[O:33])[C:32](=[CH:1][C:3]2[CH:4]=[CH:5][C:6]([O:7][C:8]3[CH:9]=[CH:10][C:11]([C:14](=[CH:18][C:19]4[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=4)[C:15]([OH:17])=[O:16])=[CH:12][CH:13]=3)=[CH:26][CH:27]=2)[S:28]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

HCID 243Benzoic AcidHCID 313Hydrochloric AcidHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 725565312-[4-(4-Formylphenoxy)-phenyl]-3-p-tolylacrylic acid

생성물 1

HCID 725565302-{4-[4-(2,4-Dioxothiazolidin-5-ylidenemethyl)-phenoxy]-phenyl}-3-p-tolylacrylic acid

시약·촉매·용매

1
HCID 1140Toluene용매

실험 절차

To a solution of 39 (4.0 g, 11.2 mmol), thiazolidine-2,4-dione (1.31 g, 11.2 mmol), and benzoic acid (1.64 g, 13.4 mmol) in 100 mL toluene was added piperidine (1.66 mL, 16.8 mmol). The mixture was vigorously refluxed with Dean Stark apparatus for 1.5 h under argon then cooled to room temperature. 5% HCl was added to pH 1. The solid was filtered, recrystallized out of toluene, filtered, and washed with hexane before drying under vacuum to a yellow solid (quantitative). 1H NMR (400 MHz, DMSO-d6) δ 12.70 (br s, 1H), 12.59 (br s, 1H), 7.80 (s, 1H), 7.75 (s, 1H), 7.67 (d, J=8.8 Hz, 2H), 7.22 (d, J=9.2 Hz, 2H), 7.18 (d, J=7.6 Hz, 2H), 7.12 (d, J=9.2 Hz, 2H), 7.07 (d, J=8.0 Hz, 2H), 6.99 (d, J=8.0 Hz, 2H), 2.25 (s, 3H).

후처리

  1. temperatureThe mixture was vigorously refluxed with Dean Stark apparatus for 1.5 h under argon
  2. filtrationThe solid was filtered
  3. customrecrystallized out of toluene
  4. filtrationfiltered
  5. washwashed with hexane
  6. custombefore drying under vacuum to a yellow solid (quantitative)

출처 및 근거

ORD 기록
ord-3fb63e21b3f1415c86fbb76c30beb392
출처 데이터셋
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07718682B2

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