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Water → 2-(3-(5-(3-Carbazol-9-ylphenyl)-1,3,4-oxadiazol-2-yl)phenoxy)ethyl methacrylate

HRID 2278476
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2278476
[CH:1]1[C:13]2[N:12]([C:14]3[CH:15]=[C:16]([C:20]4[O:24][C:23]([C:25]5[CH:26]=[C:27]([OH:31])[CH:28]=[CH:29][CH:30]=5)=[N:22][N:21]=4)[CH:17]=[CH:18][CH:19]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:32]([O:37][CH2:38][CH2:39]Br)(=[O:36])[C:33]([CH3:35])=[CH2:34].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[C:32]([O:37][CH2:38][CH2:39][O:31][C:27]1[CH:28]=[CH:29][CH:30]=[C:25]([C:23]2[O:24][C:20]([C:16]3[CH:17]=[CH:18][CH:19]=[C:14]([N:12]4[C:11]5[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=5[C:5]5[C:13]4=[CH:1][CH:2]=[CH:3][CH:4]=5)[CH:15]=3)=[N:21][N:22]=2)[CH:26]=1)(=[O:36])[C:33]([CH3:35])=[CH2:34]
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Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 782712-Bromoethyl methacrylateHCID 675158343-(5-(3-Carbazol-9-ylphenyl)-1,3,4-oxadiazol-2-yl)phenol

Produkt 1

HCID 675163412-(3-(5-(3-Carbazol-9-ylphenyl)-1,3,4-oxadiazol-2-yl)phenoxy)ethyl methacrylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

To a solution of 3-(5-(3-carbazol-9-ylphenyl)-1,3,4-oxadiazol-2-yl)phenol (0.80 g, 1.98 mmol) and 2-bromoethyl methacrylate (0.40 g, 2.07 mmol) in DMF (15.0 ml) was added K2CO3 (4.0 g, 28.94 mmol) at room temperature under stirring. The reaction was carried out at room temperature for 21 h. Water (100.0 ml) was added. Brown solid product was obtained by filtration. The crude product was purified by silica gel column chromatography using dichloromethane/ethyl acetate (9.5:0.5) as eluent. After removal of solvent, Methanol (120.0 ml) was added into this glass-like solid. After removal of methanol, White solid product was obtained and collected from water by filtration. After vacuum dry, the product as white solid in 038 g (76.4%) was obtained. 1H NMR (400 MHz, CDCl3, δ): 8.34 (m, 1H), 8.26 (m, 111), 8.15 (dd, J1=8.0 Hz, J2=0.8 Hz, 2H), 7.78-7.66 (m, 4H), 7.42 (m, 5H), 7.31 (m, 2H), 7.10 (m, 1H), 6.12 (t, J=1.2 Hz, 1H), 5.56 (m, 1H), 4.51 (m, 2H, OCH2), 4.27 (m, 2H, OCH2), 1.93 (t, 3=1.2 Hz, 3H, CH3). 13C NMR (100 MHz, CDCl3, δ): 167.25, 164.71, 163.88, 158.97, 140.61, 138.73, 135.86, 130.86, 130.37, 126.19, 125.85, 125.78, 125.43, 124.80, 123.56, 120.45, 120.37, 119.85, 118.88, 112.42, 109.54, 66.21, 62.84, 18.27. [M]+ calcd for C32H25N3O4, 515.2. found 515.2. Anal. Calcd for C32H25N3O4: C, 74.55; H, 4.89; N, 8.15. Found: C, 74.26; H, 4.83; N, 8.03.

Aufarbeitung

  1. customBrown solid product was obtained by filtration
  2. customThe crude product was purified by silica gel column chromatography
  3. customAfter removal of solvent, Methanol (120.0 ml)
  4. additionwas added into this glass-like solid
  5. customAfter removal of methanol
  6. customWhite solid product was obtained
  7. filtrationcollected from water by filtration
  8. customAfter vacuum dry

Quellen und Nachweise

ORD-Eintrag
ord-4d29e05b2dee4f3195992e1e43481aa3
Quelldatensatz
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09133177B2

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