Imidazole → (+-)-alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanol

HRID 27445

반응식

HRID 27445 반응식
[Na].[NH:2]1[CH:6]=[CH:5][N:4]=[CH:3]1.[Cl:7][C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[CH:15]([OH:18])[CH2:16]Cl.O>CO.CN(C)C=O>[Cl:7][C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[CH:15]([OH:18])[CH2:16][N:2]1[CH:6]=[CH:5][N:4]=[CH:3]1

참가 물질

7

반응물 4

HCID 795ImidazoleHCID 962WaterHCID 943512,4-Dichloro-alpha-(chloromethyl)benzenemethanolHCID 5360545Sodium

생성물 1

HCID 32238(+-)-alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanol수율 66.3%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6228Dimethylformamide용매

반응 조건

온도
40 °C

실험 절차

30 g of sodium were added to a solution of 88.5 g of imidazole in 600 ml of methanol; the solvent was then evaporated off. The residue was dissolved in 300 ml of dimethylformamide and heated to 115°-120° C. To the solution so obtained was added, dropwise and under stirring, a solution of 225 g of 1-(2',4'-dichlorophenyl)-2-chloro-ethanol in 400 ml of dimethylformamide. The mixture was heated to 115°-120° C. and maintained at that temperature for 20 minutes and, after subsequent cooling to 40° C., 2500 ml of iced water were added under vigorous stirring. The product precipitated under stirring over a period of about two hours, the upper liquid was then decanted off, a further 2500 ml of water were added and, after standing, the whole was filtered. The precipitate thus obtained was dried and crystallized from toluene. 170 g of the desired product, melting at 134°-135° C., was obtained.

후처리

  1. customthe solvent was then evaporated off
  2. dissolutionThe residue was dissolved in 300 ml of dimethylformamide
  3. temperatureheated to 115°-120° C
  4. customTo the solution so obtained
  5. additionwas added
  6. temperatureThe mixture was heated to 115°-120° C.
  7. temperaturemaintained at that temperature for 20 minutes
  8. customThe product precipitated
  9. stirringunder stirring over a period of about two hours
  10. customthe upper liquid was then decanted off
  11. additiona further 2500 ml of water were added
  12. filtrationthe whole was filtered
  13. customThe precipitate thus obtained
  14. customwas dried
  15. customcrystallized from toluene

출처 및 근거

ORD 기록
ord-f5e27aea74774ac9bd2760a0a0f55d0f
출처 데이터셋
uspto-grants-1980_09
특허 번호
US04221803

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