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

HRID 2278474Notes

Reaction equation

HRID 2278474 reaction equation
[CH:1]1[C:13]2[N:12]([C:14]3[CH:19]=[CH:18][C:17]([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:16][CH:15]=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:17]3[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][CH:16]=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 675161893-(5-(4-Carbazol-9-ylphenyl)-1,3,4-oxadiazol-2-yl)phenol

Product 1

HCID 675159522-(3-(5-(4-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-(4-carbazol-9-ylphenyl)-1,3,4-oxadiazol-2-yl)phenol (1.0 g, 2.48 mmol) and 2-bromoethyl methacrylate (0.5 g, 2.59 mmol) in DMF (20.0 ml) was added K2CO3 (4.0 g, 28.94 mmol) at room temperature under stirring. The reaction was carried out at room temperature for 23.5 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 (9.7:0.3) as eluent. After removal of solvent, white glass-like solid product was dissolved in acetone. The acetone solution was slowly dropped into methanol (60.0 ml) under stirring. After addition of acetone solution, water (30.0 ml) was added into this solution. White solid product was obtained and collected by filtration. After vacuum dry, the product as white solid in 0.98 g (76.6%) was obtained. 1H NMR (400 MHz, CDCl3, δ): 8.37 (d, J=8.0 Hz, 2H), 8.14 (dd, J1=8.0 Hz, J2=0.8 Hz, 2 Hz), 7.78-7.72 (m, 4H), 7.50-7.41 (m, 5H), 7.31 (m, 2H), 7.12 (dd, J1=8.0 Hz, J2=2.4 Hz, 1H), 6.16 (d, J=0.4 Hz, 1H, C═C—H), 5.59 (t, J=0.8 Hz, 1H, C═C—H), 4.55 (t, J=4.8 Hz, 2H, OCH2), 4.33 (t, J=4.8 Hz, 2H, OCH2), 1.96 (s, 3H, CH3). 13C NMR (100 MHz, CDCl3, δ): 167.28, 164.57, 164.06, 140.94, 140.22, 135.89, 130.40, 128.59, 127.21, 126.21, 124.97, 123.78, 122.34, 120.58, 120.47, 119.79, 118.74, 112.47, 109.87, 66.22, 62.86, 18.30. [M]+ calcd for C32H25N3O4, 515.2. found 515.2. Anal. Calcd for C32H25N3O4: C, 74.55; H, 4.89; N, 8.15. Found: C, 74.29; H, 4.79; N, 8.13.

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, white glass-like solid product
  4. dissolutionwas dissolved in acetone
  5. additionThe acetone solution was slowly dropped into methanol (60.0 ml)
  6. stirringunder stirring
  7. additionAfter addition of acetone solution, water (30.0 ml)
  8. additionwas added into this solution
  9. customWhite solid product was obtained
  10. filtrationcollected by filtration
  11. customAfter vacuum dry

Sources & evidence

ORD record
ord-ce5845a56c2b4edbb065bc8c5ad67da6
Source dataset
uspto-grants-2015_09
Patent number
US09133177B2

Reaction notes

Loading…