3-Bromo-1,1,1-trifluoro-2-propanone → 5-[1-[4-(methylsulfonyl)phenyl]-4-hydroxy-4-(trifluoromethyl)-4,5-dihydro-1H-imidazol-2-yl)-1,3-benzodioxole

HRID 1166332

反応式

HRID 1166332 の反応式
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([C:10](=[NH:22])[NH:11][C:12]3[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=3)=[CH:4][C:3]=2[O:2]1.C(=O)(O)[O-].[Na+].Br[CH2:29][C:30](=[O:35])[C:31]([F:34])([F:33])[F:32]>C(O)(C)C>[CH3:21][S:18]([C:15]1[CH:14]=[CH:13][C:12]([N:11]2[CH2:29][C:30]([OH:35])([C:31]([F:34])([F:33])[F:32])[N:22]=[C:10]2[C:5]2[CH:6]=[CH:7][C:8]3[O:9][CH2:1][O:2][C:3]=3[CH:4]=2)=[CH:17][CH:16]=1)(=[O:19])=[O:20]

参加物

5

反応物 3

HCID 790083-Bromo-1,1,1-trifluoro-2-propanoneHCID 516892Sodium BicarbonateHCID 178504792HCID 178504792、化合物

生成物 1

HCID 105986165-[1-[4-(methylsulfonyl)phenyl]-4-hydroxy-4-(trifluoromethyl)-4,5-dihydro-1H-imidazol-2-yl)-1,3-benzodioxole収率 47%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

To a mixture of 3,4-methylenedioxy-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide from Step 1 (2.32 g, 7.3 mmol) and sodium bicarbonate (1.23 g, 14.6 mmol) in isopropanol (100 mL), 3-bromo-1,1,1-trifluoroacetone (5.4 mL, 52 mmol) was added. After heating the reaction mixture to reflux for 24 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 (7.1 g) was purified by chromatography (silica gel, toluene/ethyl acetate, 1/1) to give 5-[1-[4-(methylsulfonyl)phenyl]-4-hydroxy-4-(trifluoromethyl)-4,5-dihydro-1H-imidazol-2-yl]-1,3-benzodioxole (1.46 g, 47%) as a white solid: mp 200-202° C. Anal. Calc'd. for C18H15N2SO5F3.0.25 PhCH3: C, 52.55, H, 3.80, N, 6.21. Found: C, 52.73, H, 3.78, N, 6.01.

後処理

  1. additionwas added
  2. temperatureAfter heating the reaction mixture
  3. temperatureto reflux for 24 hours
  4. customthe solvent was removed
  5. dissolutionThe residue was redissolved in methylene chloride
  6. washwashed with water
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude mixture (7.1 g) was purified by chromatography (silica gel, toluene/ethyl acetate, 1/1)

出典と根拠

ORDレコード
ord-d2b6e799376c46abacc4033cf758a33e
出典データセット
uspto-grants-2003_09
特許番号
US06613789B2

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