Sodium Bicarbonate → 1h-Imidazole,2-(4-chlorophenyl)-4-(3-fluorophenyl)-1-[4-(methylsulfonyl)phenyl]-

HRID 1166323

反応式

HRID 1166323 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(=O)(O)[O-].[Na+].[F:26][C:27]1[CH:28]=[C:29]([CH:34]=[CH:35][CH:36]=1)[C:30](=O)[CH2:31]Br>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)[CH:31]=[C:30]([C:29]3[CH:34]=[CH:35][CH:36]=[C:27]([F:26])[CH:28]=3)[N:20]=2)=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 27374513-Fluorophenacyl bromideHCID 1785047964-chloro-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide

生成物 1

HCID 221489891h-Imidazole,2-(4-chlorophenyl)-4-(3-fluorophenyl)-1-[4-(methylsulfonyl)phenyl]-収率 50.3%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

反応条件

温度
77.5 °C

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 (30 mL), 3-fluorophenacyl bromide (0.97 g, 4.48 mmol) was added. After heating the reaction mixture at 75-80° C. for 18 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 purified by chromatography (silica gel, hexane/ethyl acetate, 6/4) to give 2-(4-chlorophenyl)-4-(3-fluorophenyl)-1-[4-(methylsulfonyl)phenyl]-1H-imidazole (481 mg, 50%) as a white solid: mp 194-196° C. Anal. Calc'd. for C22H16N2SO2FCl: C, 61.90, H, 3.78, N, 6.56, S, 7.51. Found: C, 61.71, H, 3.59, N, 6.42, S, 7.69.

後処理

  1. additionwas added
  2. customthe solvent was removed
  3. dissolutionThe residue was redissolved in methylene chloride
  4. washwashed with aqueous sodium bicarbonate and water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by chromatography (silica gel, hexane/ethyl acetate, 6/4)

出典と根拠

ORDレコード
ord-303ef88f46ac42948bf696b91d41daec
出典データセット
uspto-grants-2003_09
特許番号
US06613789B2

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