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

HRID 52306

반응식

HRID 52306 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-aca2362d63d54cfc995742bd8c875585
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616601

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