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Phosphorus trichloride → 4-[5-(4-Fluorophenyl)-1-methyl-2-phenyl-1h-imidazol-4-yl]pyridin-2(1h)-one

HRID 23526
ノート
印刷プレビュー

反応式

HRID 23526 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N+:10]([O-])[C:9]=2[C:21]2[CH:26]=[CH:25][NH:24][C:23](=[O:27])[CH:22]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)Cl>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:10][C:9]=2[C:21]2[CH:26]=[CH:25][NH:24][C:23](=[O:27])[CH:22]=2)=[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

4

反応物 2

HCID 24387Phosphorus trichlorideHCID 695576504-[5-(4-fluorophenyl)-1-methyl-3-oxido-2-phenyl-1H-imidazol-4-yl]pyridin-2(1H)-one

生成物 1

HCID 225741694-[5-(4-Fluorophenyl)-1-methyl-2-phenyl-1h-imidazol-4-yl]pyridin-2(1h)-one収率 40.7%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
60 °C

実験手順

To a solution of 4-[5-(4-fluorophenyl)-1-methyl-3-oxido-2-phenyl-1H-imidazol-4-yl]pyridin-2(1H)-one of Step A (56 mg, 0.155 mmol) in CHCl3 (2 mL) was added phosphorous trichloride (16 μL, 0.186 mmol) dropwise at room temperature. The reaction mixture was heated at 60° C. for 2 hours, cooled, and poured into 1N NaOH/ice solution. The aqueous layer was extracted with CH2Cl2, and the combined organic extracts were washed with H2O followed by brine. After drying over Na2SO4, the solvent was removed in vacuo. The crude material was purified by preparative thin layer chromatography (1:10 MeOH:CH2Cl2 as an eluent) to obtain 21.8 mg of the title compound.

後処理

  1. temperaturecooled
  2. extractionThe aqueous layer was extracted with CH2Cl2
  3. washthe combined organic extracts were washed with H2O
  4. dry with materialAfter drying over Na2SO4
  5. customthe solvent was removed in vacuo
  6. customThe crude material was purified by preparative thin layer chromatography (1:10 MeOH

出典と根拠

ORDレコード
ord-d536d149bf6e440b94ffa5ef2b01369e
出典データセット
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06852727B2

反応ノート

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