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Water → 2-[5-(4-chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-ethyl-1H-pyrazol-3-yl]-3-methyl-3,5-dihydro-imidazol-4-one

HRID 1805207
ノート
印刷プレビュー

反応式

HRID 1805207 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[NH:25][C:24](=[O:26])[CH2:23][N:22]=3)[C:9]=2[CH2:27][CH3:28])=[CH:4][CH:3]=1.[C:29](=O)([O-])[O-].[K+].[K+].CI.O>C(#N)C>[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:25]([CH3:29])[C:24](=[O:26])[CH2:23][N:22]=3)[C:9]=2[CH2:27][CH3:28])=[CH:4][CH:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 593171472-[5-(4-chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-ethyl-1H-pyrazol-3-yl]-3,5-dihydro-imidazol-4-one

生成物 1

HCID 593171542-[5-(4-chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-ethyl-1H-pyrazol-3-yl]-3-methyl-3,5-dihydro-imidazol-4-one収率 68%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
60 °C

実験手順

To a solution of 26 (100 mg, 0.23 mmol) in acetonitrile (8 mL) at room temperature was sequentially added potassium carbonate (150 mg, 1.09 mole) and methyl iodide (2 g, 14.08 mmol) slowly. The mixture was stirred at 60° C. for 6 h. Water was added and the resulting mixture was extracted with ethyl acetate (2×50 mL). The combined extracts were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. Purification of the crude residue by flash chromatography on silica gel eluting with hexanes/ethyl acetate (1:1) gave the compound 29 (70 mg, 68%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.45 (d, 1H), 7.30 (d, 2H), 7.25 (dd, 1H), 7.18 (d, 1H), 7.09 (d, 2H), 4.88 (s, 0.82H), 4.51 (s, 1.18H), 3.42 (s, 1.77H), 3.24 (s, 1.23H), 2.65 (q, 2H), 1.15 (t, 3H); ESMS m/: 447.0 (M+1).

後処理

  1. customat room temperature
  2. extractionthe resulting mixture was extracted with ethyl acetate (2×50 mL)
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the crude residue by flash chromatography on silica gel eluting with hexanes/ethyl acetate (1:1)

出典と根拠

ORDレコード
ord-e55db8be060c464aa726e69ec4990574
出典データセット
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08354442B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート