3-Bromo-1,1,1-trifluoro-2-propanone → 2-(4-methylphenyl)-4-hydroxy-1-(4-(methylsulfonyl)phenyl]-4-trifluoromethyl-4,5-dihydro-1H-imidazole

HRID 1352959

反応式

HRID 1352959 の反応式
[CH3:1][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+].Br[CH2:27][C:28](=[O:33])[C:29]([F:32])([F:31])[F:30]>C(O)(C)C>[CH3:1][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:18])=[O:17])=[CH:12][CH:11]=3)[CH2:27][C:28]([OH:33])([C:29]([F:32])([F:31])[F:30])[N:20]=2)=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 790083-Bromo-1,1,1-trifluoro-2-propanoneHCID 516892Sodium BicarbonateHCID 178425632HCID 178425632、化合物

生成物 1

HCID 105249012-(4-methylphenyl)-4-hydroxy-1-(4-(methylsulfonyl)phenyl]-4-trifluoromethyl-4,5-dihydro-1H-imidazole収率 47.3%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

To a mixture of 4-methyl-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide (step 1) (5 g, 17.4 mmol) and sodium bicarbonate (2.9 g, 34.7 mmol) in isopropanol (200 mL), 3-bromo-1,1,1-trifluoroacetone (3.6 ml, 34.7 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 water. The organic fractions were combined, dried over sodium sulfate, filtered and concentrated in vacuo. The crude mixture (8.9 g) was purified by chromatography (silica gel, toluene/ethyl acetate 6/4) to give 2-(4-methylphenyl)-4-hydroxy-1-[4-(methylsulfonyl)phenyl]-4-trifluoromethyl-4,5-dihydro-1H-imidazole (3.28 g, 47%) as a white solid: mp 198–199° C. Anal. Calc'd for C18H17N2F3SO3.0.3 PhMe C, 56.67; H, 4.59; N, 6.58. Found: C, 56.95; H, 4.68; N, 6.13.

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 water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude mixture (8.9 g) was purified by chromatography (silica gel, toluene/ethyl acetate 6/4)

出典と根拠

ORDレコード
ord-e5e13a1e1cd84e16938d18ffeb9f819e
出典データセット
uspto-grants-2007_05
特許番号
US07220770B2

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