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

HRID 1846300ノート

反応式

HRID 1846300 の反応式
[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]

参加物

5

反応物 2

HCID 289325784-(2-Hydroxyethoxy)-3,5-dimethylbenzaldehydeHCID 86659806HCID 86659806、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 24014Cupric Chloride触媒HCID 702Ethanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1af68a9878d243a2847134561cf4dd0a
出典データセット
uspto-grants-2015_02
特許番号
US08952021B2

反応ノート

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