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

HRID 52313

반응식

HRID 52313 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:9](=[NH:21])[NH:10][C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].C(=O)(O)[O-].[Na+].Br[CH2:28][C:29](=[O:34])[C:30]([F:33])([F:32])[F:31]>C(O)(C)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]([C:11]3[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:18])=[O:19])=[CH:13][CH:12]=3)[CH2:28][C:29]([OH:34])([C:30]([F:33])([F:32])[F:31])[N:21]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]

참가 물질

5

반응물 3

HCID 790083-Bromo-1,1,1-trifluoro-2-propanoneHCID 516892Sodium BicarbonateHCID 178425633HCID 178425633, 화합물

생성물 1

HCID 117970112-(3-chloro-4-methylphenyl)-4-hydroxy-1-(4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-4,5-dihydro-1H-imidazole수율 25%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

To a mixture of 3-chloro-4-methyl-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide from Step 1 (2.35 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 to reflux the reaction mixture 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 (7.3 g) was chromatographed (silica gel, toluene/ethyl acetate, 1/1) to give 2-(3-chloro-4-methylphenyl)-4-hydroxy-1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-4,5-dihydro-1H-imidazole (0.79 g, 25%) as a white solid: mp 201° C. Anal. Calc'd. for C18H16N2SO3F3Cl.0.5 PhCH3 : C, 53.92, H, 4.21, N, 5.81. Found: C, 54.20, H, 4.19, N, 5.67.

후처리

  1. additionwas added
  2. temperatureAfter heating
  3. temperatureto reflux the reaction mixture 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 (7.3 g) was chromatographed (silica gel, toluene/ethyl acetate, 1/1)

출처 및 근거

ORD 기록
ord-04ba7be7027449f1917830c4eb03946d
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616601

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