2-氯苄溴 → 1H-Imidazole, 2-butyl-1-[(2-chlorophenyl)methyl]-

HRID 36969笔记

反应方程式

HRID 36969 反应方程式
[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]

参与物

5

反应物 3

HCID 119052-氯苄溴HCID 10942334甲醇钠HCID 118153512-丁基咪唑

产物 1

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

试剂、催化剂与溶剂 1

HCID 887(5BETA,17BETA)-17-羟基-17-(甲基-D3)-2'H-雄甾-2-烯并[3,2-C]吡唑-5'(1'H)-酮溶剂

反应条件

温度
50 °C

实验过程

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.

后处理

  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

来源与证据

ORD记录
ord-72c02d888f2d4a56b563bac835b9390c
来源数据集
uspto-grants-1995_05
专利号
US05418250

反应笔记

加载中…