Lawesson's reagent → 2-[5-(4-chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-1H-pyrazol-3-yl]-1,5,5-trimethyl-1,5-dihydro-imidazole-4-thione

HRID 1805200노트

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HRID 1805200 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=[C:10]([C:21]3[N:22]([CH3:29])[C:23]([CH3:28])([CH3:27])[C:24](=O)[N:25]=3)[C:9]=2[CH3:30])=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:40])=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=[C:10]([C:21]3[N:22]([CH3:29])[C:23]([CH3:28])([CH3:27])[C:24](=[S:40])[N:25]=3)[C:9]=2[CH3:30])=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 87949Lawesson's reagentHCID 441917474H-Imidazol-4-one, 2-[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl]-1,5-dihydro-1,5,5-trimethyl-

생성물 1

HCID 441918112-[5-(4-chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-1H-pyrazol-3-yl]-1,5,5-trimethyl-1,5-dihydro-imidazole-4-thione수율 77%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
60 °C

실험 절차

To a solution of compound 6 (98 mg, 0.22 mmol) in toluene (5 mL) was added Lawesson's reagent (150 mg, 0.37 mmol) in one portion. The resulting mixture was heated at 60° C. for 4 h, then poured into ice water. The resulting mixture was extracted with ethyl acetate (2×30 mL). The combined extracts were washed with water, saturated aqueous sodium bicarbonate, and brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography on silica gel with hexanes/ethyl acetate (7:3) to give the desired thioketone 21 (78 mg, 77%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.48 (d, 1H), 7.32 (d, 2H), 7.28 (dd, 1H), 7.22 (d, 1H), 7.08 (d, 2H), 3.62 (s, 3H), 2.48 (s, 3H), 1.55 (s, 6H); ESMS m/z: 477.0 (M+1).

후처리

  1. extractionThe resulting mixture was extracted with ethyl acetate (2×30 mL)
  2. washThe combined extracts were washed with water, saturated aqueous sodium bicarbonate, and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography on silica gel with hexanes/ethyl acetate (7:3)

출처 및 근거

ORD 기록
ord-2740fb5741b144eca356a075d576303b
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354442B2

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