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

HRID 1248989
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HRID 1248989 반응식
[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
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참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매
HCID 8857
Ethyl Acetate
용매

실험 절차

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##

후처리

  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)

출처 및 근거

ORD 기록
ord-d6160d4a3b514b19a31cf99836d87d83
출처 데이터셋
uspto-grants-1986_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04628104

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