p-Toluenesulfonic acid monohydrate → 2-Benzo[1,3]dioxol-5-yl-1-(4-methanesulfonyl-phenyl)-4-trifluoromethyl-1H-imidazole

HRID 1166333ノート

反応式

HRID 1166333 の反応式
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:15][C:14](O)([C:16]([F:19])([F:18])[F:17])[N:13]=[C:12]2[C:21]2[CH:29]=[CH:28][C:24]3[O:25][CH2:26][O:27][C:23]=3[CH:22]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[N:13]=[C:12]2[C:21]2[CH:29]=[CH:28][C:24]3[O:25][CH2:26][O:27][C:23]=3[CH:22]=2)=[CH:9][CH:10]=1)(=[O:4])=[O:3]

参加物

4

反応物 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 105986165-[1-[4-(methylsulfonyl)phenyl]-4-hydroxy-4-(trifluoromethyl)-4,5-dihydro-1H-imidazol-2-yl)-1,3-benzodioxole

生成物 1

HCID 107876982-Benzo[1,3]dioxol-5-yl-1-(4-methanesulfonyl-phenyl)-4-trifluoromethyl-1H-imidazole収率 80%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A mixture of 5-[1-[4-(methylsulfonyl)phenyl]-4-hydroxy-4-(trifluoromethyl)-4,5-dihydro-1H-imidazol-2-yl]-1,3-benzodioxole from Step 2 (1.26 g, 2.9 mmol) and p-toluenesulfonic acid monohydrate (200 mg) in toluene (50 mL) was heated to reflux for 72 hours. The reaction mixture was cooled and the solvent removed under reduced pressure. The crude residue was redissolved in methylene chloride and washed with water, aqueous sodium bicarbonate and brine. After drying (Na2SO4), filtration and concentration in vacuo, the crude mixture (1.34 g) was purified by chromatography on silica gel using toluene/ethyl acetate 1/1 to give pure 5-[1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-1H-imidazol-2-yl]-1,3-benzodioxole (940 mg, 80%) as a white solid: mp (DSC) 165° C. Anal Calc'd. for C18H13N2SO4F3: C, 52.68, H, 3.19, N, 6.83. Found: C, 53.05, H, 3.19, N, 6.65.

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 72 hours
  3. temperatureThe reaction mixture was cooled
  4. customthe solvent removed under reduced pressure
  5. dissolutionThe crude residue was redissolved in methylene chloride
  6. washwashed with water, aqueous sodium bicarbonate and brine
  7. customAfter drying
  8. filtration(Na2SO4), filtration and concentration in vacuo
  9. customthe crude mixture (1.34 g) was purified by chromatography on silica gel

出典と根拠

ORDレコード
ord-65fa7f2a2ba14f0499749955afbba73c
出典データセット
uspto-grants-2003_09
特許番号
US06613789B2

反応ノート

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