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Imidazole → 1-(2,4-Dichlorophenyl)-3-(imidazol-1-yl)-2-phenylpropan-1-one

HRID 1248989
ノート
印刷プレビュー

反応式

HRID 1248989 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:18])[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[CH2:11].[NH:19]1[CH:23]=[CH:22][N:21]=[CH:20]1.CN(C)C(=N)N(C)C>O1CCCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:18])[CH:10]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH2:11][N:19]1[CH:23]=[CH:22][N:21]=[CH:20]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 795ImidazoleHCID 664601,1,3,3-TetramethylguanidineHCID 1294381-(2,4-Dichlorophenyl)-2-phenylpropen-1-one

生成物 1

HCID 137499421-(2,4-Dichlorophenyl)-3-(imidazol-1-yl)-2-phenylpropan-1-one収率 12%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒
HCID 8857
Ethyl Acetate
溶媒

実験手順

A solution of 1-(2,4-dichlorophenyl)-2-phenylpropen-1-one (4 g), imidazole (1.36 g) and tetramethylguanidine (0.5 ml) in tetrahydrofuran (100 ml) was heated at reflux for 12 hours. The reaction mixture was cooled and concentrated under reduced pressure to yield a gum. The gum was dissolved in ethyl acetate, washed with distilled water, and acidified with 4N hydrochloric acid. The resulting aqueous phase was basified with sodium hydrogen carbonate and extracted with ethyl acetate. The organic phase was separated, washed with distilled water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to yield an oil which was chromatographed on silica gel in methanol/dichloromethane (1:9) to yield 1-(2,4-dichlorophenyl)-3-(imidazol-1-yl)-2-phenylpropan-1-one (600 mg), which was treated with ethereal hydrogen chloride to yield the hydrochloride salt of 1-(2,4-dichlorophenyl)-3-(imidazol-1-yl)-2-phenylpropan-1-one, m.p. 110° C., (Found: C, 55.38; H, 4.37; N, 7.40; C18H15Cl3N2O.1/2H2O requires C, 55.34; H, 4.13; N, 7.17) having the formula: ##STR12##

後処理

  1. temperatureat reflux for 12 hours
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated under reduced pressure
  4. customto yield a gum
  5. washwashed with distilled water
  6. extractionextracted with ethyl acetate
  7. customThe organic phase was separated
  8. washwashed with distilled water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customto yield an oil which
  12. customwas chromatographed on silica gel in methanol/dichloromethane (1:9)

出典と根拠

ORDレコード
ord-d6160d4a3b514b19a31cf99836d87d83
出典データセット
uspto-grants-1986_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04628104

反応ノート

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