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

HRID 2278476Notes

Reaction equation

HRID 2278476 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4d29e05b2dee4f3195992e1e43481aa3
Source dataset
uspto-grants-2015_09
Patent number
US09133177B2

Reaction notes

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