4-(2-Hydroxyethoxy)-3,5-dimethylbenzaldehyde → 3-(4-sec-butylphenyl)-2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)-6-(methylsulfonyl)quinazolin-4(3H)-one

HRID 1846300Notes

Reaction equation

HRID 1846300 reaction equation
[NH2:1][C:2]1[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH2:15][CH3:16])[CH3:14])=[CH:9][CH:8]=1)=[O:5].[OH:25][CH2:26][CH2:27][O:28][C:29]1[C:36]([CH3:37])=[CH:35][C:32]([CH:33]=O)=[CH:31][C:30]=1[CH3:38]>C(O)C.[Cu](Cl)Cl>[CH:13]([C:10]1[CH:9]=[CH:8][C:7]([N:6]2[C:4](=[O:5])[C:3]3[C:2](=[CH:20][CH:19]=[C:18]([S:21]([CH3:24])(=[O:23])=[O:22])[CH:17]=3)[N:1]=[C:33]2[C:32]2[CH:35]=[C:36]([CH3:37])[C:29]([O:28][CH2:27][CH2:26][OH:25])=[C:30]([CH3:38])[CH:31]=2)=[CH:12][CH:11]=1)([CH2:15][CH3:16])[CH3:14]

Participants

5

Reactant 2

HCID 289325784-(2-Hydroxyethoxy)-3,5-dimethylbenzaldehydeHCID 86659806HCID 86659806, compound

Product 1

HCID 468410063-(4-sec-butylphenyl)-2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)-6-(methylsulfonyl)quinazolin-4(3H)-one

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-amino-N-(4-sec-butyl-phenyl)-5-methanesulfonyl-benzamide (0.21 g, 0.58 mmol) and 4-(2-hydroxy-ethoxy)-3,5-dimethyl-benzaldehyde (0.13 g, 0.64 mmol) in anhydrous ethanol (20 mL) was added anhydrous copper (II) chloride (0.440 g, 3.27 mmol) and the reaction mixture was refluxed for 48 hours. The solvent was evaporated in vacuo and the product was extracted with dichloromethane. The solvent was evaporated in vacuo and the residue was triturated with ether and methanol/ethyl acetate and filtered off, to obtain the title compound as a white solid. Yield: 0.13 g (43%). MP 258.8-260.2° C. 1H-NMR (400 MHz, CDCl3): δ 8.94 (s, 1H), 8.28 (d, 1H), 7.94 (d, 1H), 7.19 (m, 2H), 7.03 (m, 2H), 7.01 (s, 2H), 3.91 (m, 2H), 3.79 (d, 2H), 3.17 (s, 3H), 2.58 (m, 1H), 2.18 (s, 3H), 2.03 (m, 1H), 1.60 (m, 2H), 1.21 (d, 3H), 0.78 (t, 3H). MS (ES+) m/z: 521.66 (M+1).

Workup

  1. temperaturethe reaction mixture was refluxed for 48 hours
  2. customThe solvent was evaporated in vacuo
  3. extractionthe product was extracted with dichloromethane
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was triturated with ether and methanol/ethyl acetate
  6. filtrationfiltered off

Sources & evidence

ORD record
ord-1af68a9878d243a2847134561cf4dd0a
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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