Bromomethyl 4-methoxyphenyl ketone → 2-(4-chlorophenyl)-4-(4-methoxyphenyl)-1-(4-(methylsulfonyl)phenyl]-4-(4-methoxyphenyl)-1H-imidazole

HRID 52306

反応式

HRID 52306 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[NH:20])[NH:9][C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[C:21](=[O:24])(O)[O-].[Na+].[CH3:26][O:27][C:28]1[CH:37]=[CH:36][C:31]([C:32](=O)[CH2:33]Br)=[CH:30][CH:29]=1>C(O)(C)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]([C:10]3[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:17])=[O:18])=[CH:12][CH:11]=3)[CH2:33][C:32]([C:2]3[CH:7]=[CH:6][C:5]([O:24][CH3:21])=[CH:4][CH:3]=3)([C:31]3[CH:36]=[CH:37][C:28]([O:27][CH3:26])=[CH:29][CH:30]=3)[N:20]=2)=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 516892Sodium BicarbonateHCID 1785047964-chloro-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide

生成物 1

HCID 229980782-(4-chlorophenyl)-4-(4-methoxyphenyl)-1-(4-(methylsulfonyl)phenyl]-4-(4-methoxyphenyl)-1H-imidazole収率 113.4%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

To a mixture of 4-chloro-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide (Example 1, Step 1) (700 mg, 2.24 mmol) and sodium bicarbonate (376 mg, 4.48 mmol) in isopropanol (50 mL), 4-methoxyphenacyl bromide (1.03 g, 4.48 mmol) was added. After heating the reaction mixture at 75°-80° C. for 20 hours, the solvent was removed. The residue was redissolved in methylene chloride and washed with aqueous sodium bicarbonate and water. The organic fractions were combined, dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was chromatographed (silica gel, hexane/ethyl acetate, 6/4) to give 2-(4-chlorophenyl)-4-(4-methoxyphenyl)-1-[4-(methylsulfonyl)phenyl]-4-(4-methoxyphenyl)-1H-imidazole (695 mg, 71%) as a white solid: mp 110°-113° C. Anal Calc'd. for C23H19N2SO3Cl: C, 62.94, H, 4.36, N, 6.38, S, 7.30. Found: C, 62.54, H, 4.43, N, 6.17, S, 7.15.

後処理

  1. additionwas added
  2. temperatureAfter heating the reaction mixture at 75°-80° C. for 20 hours
  3. customthe solvent was removed
  4. dissolutionThe residue was redissolved in methylene chloride
  5. washwashed with aqueous sodium bicarbonate and water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was chromatographed (silica gel, hexane/ethyl acetate, 6/4)

出典と根拠

ORDレコード
ord-aca2362d63d54cfc995742bd8c875585
出典データセット
uspto-grants-1997_04
特許番号
US05616601

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