p-Toluenesulfonic acid monohydrate → 1-(4-Methanesulfonyl-phenyl)-2-thiophen-3-yl-4-trifluoromethyl-1H-imidazole

HRID 1166379노트

반응식

HRID 1166379 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[CH:21]=[CH:20][S:19][CH:18]=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:24])([F:25])[F:23])[N:3]=[C:4]2[C:17]2[CH:21]=[CH:20][S:19][CH:18]=2)=[CH:12][CH:11]=1)(=[O:15])=[O:14]

참가 물질

4

반응물 2

HCID 521998p-Toluenesulfonic acid monohydrate2회HCID 22998113HCID 22998113, 화합물

생성물 1

HCID 106192741-(4-Methanesulfonyl-phenyl)-2-thiophen-3-yl-4-trifluoromethyl-1H-imidazole수율 64%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A mixture of the 4,5-dihydro-imidazole of step 2 (1.5 g, 3.8 mmol) and p-toluenesulfonic acid monohydrate (0.30 g, 1.5 mmol) in toluene (250 ml) was heated to reflux for 40 hours. An additional p-toluenesulfonic acid monohydrate (0.15 g, 0.78 mmol) was added. The reaction mixture was heated to reflux for 18 hours. The reaction mixture was cooled and the solvent removed under reduced pressure. The crude mixture (3.5 g) was purified by chromatography on silica gel using ethyl acetate/toluene (55/45) to give pure 3-[1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-1H-imidazol-2-yl]thiophene (0.90 g, 64%) as a white solid: mp 194-197° C. Anal. Calc'd. for C15H11N2S2O2F3: C, 48.38, H, 2.98, N. 7.52, S, 17.22. Found: C, 48.74, H, 2.98, N. 7.56, S, 17.45

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 40 hours
  3. temperatureThe reaction mixture was heated
  4. temperatureto reflux for 18 hours
  5. temperatureThe reaction mixture was cooled
  6. customthe solvent removed under reduced pressure
  7. customThe crude mixture (3.5 g) was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-00f718970968441990af442f1d319707
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06613789B2

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