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 1805200ノート

反応式

HRID 1805200 の反応式
[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

参加物

4

反応物 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-

生成物 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-thione収率 77%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-2740fb5741b144eca356a075d576303b
出典データセット
uspto-grants-2013_01
特許番号
US08354442B2

反応ノート

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