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

HRID 2278475Notes

Reaction equation

HRID 2278475 reaction equation
[CH:1]1[C:13]2[N:12]([C:14]3[CH:15]=[C:16]([C:33]4[O:37][C:36]([C:38]5[CH:39]=[C:40]([OH:44])[CH:41]=[CH:42][CH:43]=5)=[N:35][N:34]=4)[CH:17]=[C:18]([N:20]4[C:32]5[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=5[C:26]5[C:21]4=[CH:22][CH:23]=[CH:24][CH:25]=5)[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:45]([O:50][CH2:51][CH2:52]Br)(=[O:49])[C:46]([CH3:48])=[CH2:47].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[C:45]([O:50][CH2:51][CH2:52][O:44][C:40]1[CH:41]=[CH:42][CH:43]=[C:38]([C:36]2[O:37][C:33]([C:16]3[CH:15]=[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:19]=[C:18]([N:20]4[C:32]5[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=5[C:26]5[C:21]4=[CH:22][CH:23]=[CH:24][CH:25]=5)[CH:17]=3)=[N:34][N:35]=2)[CH:39]=1)(=[O:49])[C:46]([CH3:48])=[CH2:47]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 782712-Bromoethyl methacrylateHCID 675165223-(5-(3,5-Dicarbazol-9-ylphenyl)-1,3,4-oxadiazol-2-yl)phenol

Product 1

HCID 675159172-(3-(5-(3,5-Dicarbazol-9-ylphenyl)-1,3,4-oxadiazol-2-yl)phenoxy)ethyl methacrylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(5-(3,5-dicarbazol-9-ylphenyl)-1,3,4-oxadiazol-2-yl)phenol (0.7 g, 1.23 mmol) and 2-bromoethyl methacrylate (0.25 g, 1.30 mmol) in DMF (20.0 ml) was added K2CO3 (2.0 g, 14.47 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 and washed with methanol. The crude product was purified by silica gel column chromatography using dichloromethane/ethyl acetate (9.5:0.5) as eluent. After removal of solvent, white glass-like solid product was dissolved in THF (10.0 ml). Methanol (120.0 ml) was added into THF solution. White solid product was obtained and collected by filtration. After vacuum dry, the product as white solid in 0.7 g (83.3%) was obtained. 1H NMR (400 MHz, CDCl3, δ): 8.47 (d, 5=1.6 Hz, 2H), 8.16 (d, J=8.0 Hz, 4 Hz), 8.01 (d, J=1.6 Hz, 1H), 7.71 (dt, J1=8.0 Hz, J2=1.6 Hz, 1H), 7.67 (m, 1H), 7.57 (d, J=8.4 Hz, 4H), 7.49-7.40 (m, 5H), 7.34 (m, 4H), 7.10 (m, 1H), 6.11 (t, 5=1.2 Hz, 1H), 5.55 (m, 1H), 4.49 (t, J=4.4 Hz, 2H, OCH2), 4.29 (t, J=4.4 Hz, 2H, OCH2), 1.92 (t, J=1.2 Hz, 3H, CH3). 13C NMR (100 MHz, CDCl3, δ): 167.24, 165.05, 163.35, 159.01, 140.51, 140.32, 135.85, 130.43, 128.12, 127.36, 126.43, 126.16, 124.60, 123.84, 123.77, 120.82, 120.61, 119.95, 119.09, 112.50, 109.52, 66.24, 62.81, 18.26. [M]+ calcd for C44H32N4O4, 680.2.2. found 680.2. Anal. Calcd for C44H32N4O4: C, 77.63; H, 4.74; N, 8.23. Found: C, 77.49; H, 4.69; N, 8.21.

Workup

  1. customBrown solid product was obtained by filtration
  2. washwashed with methanol
  3. customThe crude product was purified by silica gel column chromatography
  4. customAfter removal of solvent, white glass-like solid product
  5. dissolutionwas dissolved in THF (10.0 ml)
  6. additionMethanol (120.0 ml) was added into THF solution
  7. customWhite solid product was obtained
  8. filtrationcollected by filtration
  9. customAfter vacuum dry

Sources & evidence

ORD record
ord-8cec6780f7d44d4ab086d8aacc16b6bb
Source dataset
uspto-grants-2015_09
Patent number
US09133177B2

Reaction notes

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