alpha-Bromo-o-chlorotoluene → 1H-Imidazole, 2-butyl-1-[(2-chlorophenyl)methyl]-

HRID 36969

反応式

HRID 36969 の反応式
[CH2:1]([C:5]1[NH:6][CH:7]=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].C[O-].[Na+].[Cl:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16]Br>CO>[CH2:1]([C:5]1[N:6]([CH2:16][C:15]2[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=2[Cl:13])[CH:7]=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

参加物

5

反応物 3

HCID 11905alpha-Bromo-o-chlorotolueneHCID 10942334Sodium MethoxideHCID 118153512-butyl-1H-imidazole

生成物 1

HCID 103773571H-Imidazole, 2-butyl-1-[(2-chlorophenyl)methyl]-収率 61.3%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
50 °C

実験手順

2-n-Butylimidazole (9.7 g, 0.078 mol) was dissolved in methanol (50 mL) and added dropwise to a solution of sodium methoxide (from sodium hydride (2.31 g, 0.0934 mol) in methanol (250 mL)). After one hour the solution was evaporated to dryness, and the sodium salt was taken up in dry dimethylformamide (150 mL) and 2-chlorobenzyl bromide (16.3 g, 0.079 mol) was added. The mixture was heated at 50° C. for 17 hours under argon, poured onto ice water and the product was extracted into ethyl acetate. The extract was washed, dried, and concentrated to give 18.5 g of crude product which was chromatographed over silica gel with 2:1 ethyl acetate/hexane to provide 11.9 g (61%) of 2-n-butyl-1-(2-chlorophenyl)methyl-1H-imidazole as an oil. Thin layer chromatography on silica gel with 4:1 ethyl acetate/hexane gave an Rf value of 0.59.

後処理

  1. customAfter one hour the solution was evaporated to dryness
  2. additionpoured onto ice water
  3. extractionthe product was extracted into ethyl acetate
  4. washThe extract was washed
  5. customdried
  6. concentrationconcentrated
  7. customto give 18.5 g of crude product which
  8. customwas chromatographed over silica gel with 2:1 ethyl acetate/hexane

出典と根拠

ORDレコード
ord-72c02d888f2d4a56b563bac835b9390c
出典データセット
uspto-grants-1995_05
特許番号
US05418250

関連ノート

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