1-溴-4-氯丁烷 → 1,2-bis[N-(4-chlorobutyl)-N-propionylamino]benzene

HRID 6186

反应方程式

HRID 6186 反应方程式
[C:1]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH:12][C:13](=[O:16])[CH2:14][CH3:15])(=[O:4])[CH2:2][CH3:3].Br[CH2:18][CH2:19][CH2:20][CH2:21][Cl:22]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.[OH-].[Na+]>[Cl:22][CH2:21][CH2:20][CH2:19][CH2:18][N:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]([C:13](=[O:16])[CH2:14][CH3:15])[CH2:18][CH2:19][CH2:20][CH2:21][Cl:22])[C:1](=[O:4])[CH2:2][CH3:3]

参与物

6

反应物 2

HCID 813641-溴-4-氯丁烷HCID 694922N-[2-(propanoylamino)phenyl]propanamide

产物 1

HCID 190792541,2-bis[N-(4-chlorobutyl)-N-propionylamino]benzene收率 12.6%

试剂、催化剂与溶剂 3

HCID 74236四丁基溴化铵催化剂HCID 1140甲苯溶剂HCID 14798二甲基对苯二胺二盐酸溶剂

实验过程

To a suspension of 3.27 g (15 mmol) of 1,2-di-propionylaminobenzene, 4.32 ml (37.5 mmol) of 4-bromo-1-chlorobutane, and 0.96 g (3.0 mmol) of tetrabutylammonium bromide in 25 ml of toluene, 5.6 ml of 50% aqueous sodium hydroxide was added at room temperature, and the mixture was stirred for 16 hours. The organic layer was separated, washed with saturated aqueous sodium chloride, and dried. The solvent was distilled off and the residue was purified by column chromatography (eluent: hexane/ethyl acetate =2 :1 to 1:1 to 1:2 to 1:4) to give 0.76 g of the desired product (12.6% yield, white crystals).

后处理

  1. additionwas added at room temperature
  2. customThe organic layer was separated
  3. washwashed with saturated aqueous sodium chloride
  4. customdried
  5. distillationThe solvent was distilled off
  6. customthe residue was purified by column chromatography (eluent: hexane/ethyl acetate =2 :1 to 1:1 to 1:2 to 1:4)

来源与证据

ORD记录
ord-100d3d0cc94243f9be6bff4a345d975c
来源数据集
uspto-grants-1993_09
专利号
US05246948

关联笔记

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