反应 #1702116

ord-003dbe4c8da8459f95df39b55fd09568

反应方程式

Nc1cccc(CNc2nc(Cl)ncc2Cl)c1
N-(3-aminobenzyl)-2,5-dichloropyrimidin-4-amine
Cl
hydrogen chloride
CCN(CC)CC
triethylamine
O=[N+]([O-])c1cccc(S(=O)(=O)Cl)c1
m-nitrobenzenesulfonyl chloride
O=[N+]([O-])c1cccc(S(=O)(=O)Nc2cccc(CNc3nc(Cl)ncc3Cl)c2)c1
desired product
收率 95.0%
O=[N+]([O-])c1cccc(S(=O)(=O)Nc2cccc(CNc3nc(Cl)ncc3Cl)c2)c1
N-(3-{[(2,5-Dichloropyrimidin-4-yl)amino]methyl}phenyl)-3-nitrobenzenesulfonamide
收率 95.0%

溶剂

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    其他the solvent was removed under vacuum
  2. 2
    workup.ADDITIONThe residue was treated with EtOAc and water
  3. 3
    干燥The organic layer was dried over Na2SO4
  4. 4
    过滤filtered
  5. 5
    浓缩concentrated under vacuum

实验过程

To a mixture of N-(3-aminobenzyl)-2,5-dichloropyrimidin-4-amine.hydrogen chloride (0.20 g, 0.58 mmol) and triethylamine (0.32 mL, 2.3 mmol) in THF (3 mL) was added slowly m-nitrobenzenesulfonyl chloride (0.13 g, 0.58 mmol). The resulting mixture was stirred at rt for 2 hours and the solvent was removed under vacuum. The residue was treated with EtOAc and water. The organic layer was dried over Na2SO4, filtered, and concentrated under vacuum to provide the desired product (0.30 g, 95%). LCMS for C17H14Cl2N5O4S (M+H)+: m/z=453.9, 455.9.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US08765727B2uspto-grants-2014_07