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

HRID 27445

反応式

HRID 27445 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
40 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f5e27aea74774ac9bd2760a0a0f55d0f
出典データセット
uspto-grants-1980_09
特許番号
US04221803

関連ノート

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