p-Toluenesulfonic acid monohydrate → 1-(4-Methanesulfonyl-phenyl)-2-thiophen-2-yl-4-trifluoromethyl-1H-imidazole

HRID 1166378노트

반응식

HRID 1166378 반응식
O[C:2]1([C:22]([F:25])([F:24])[F:23])[CH2:6][N:5]([C:7]2[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][CH:8]=2)[C:4]([C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)=[N:3]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:16][S:13]([C:10]1[CH:9]=[CH:8][C:7]([N:5]2[CH:6]=[C:2]([C:22]([F:25])([F:24])[F:23])[N:3]=[C:4]2[C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)=[CH:12][CH:11]=1)(=[O:14])=[O:15]

참가 물질

4

반응물 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 229979092-[4-Hydroxy-1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-4,5-dihydro-1h-imidazol-2-yl]thiophene

생성물 1

HCID 117936321-(4-Methanesulfonyl-phenyl)-2-thiophen-2-yl-4-trifluoromethyl-1H-imidazole수율 82%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A mixture of the 4,5-dihydro-imidazole of step 2 (0.60 g, 1.54 mmol) and p-toluenesulfonic acid monohydrate (0.12 g, 0.63 mmol) in toluene (100 ml) was heated to reflux for 4.5 hours. The reaction mixture was cooled and the solvent removed under reduced pressure. The crude mixture (1.2 g) was purified by chromatography on silica gel using ethyl acetate/hexane 50/50 to give pure 2-[1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-1H-imidazol-2-yl]thiophene (0.47 g, 82%) as a white solid: mp (DSC) 182° C. Anal. Calc'd. for C15H11N2S2O2F3 C, 48.38, H, 2.98, N, 7.52, S, 17.22. Found: C, 48.36, H, 3.02, N, 7.42, S, 17.47.

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 4.5 hours
  3. temperatureThe reaction mixture was cooled
  4. customthe solvent removed under reduced pressure
  5. customThe crude mixture (1.2 g) was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-7e5cc1d938654f6c8d33455f31661d6f
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06613789B2

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