聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯] → 2,3-二氯-N-甲基马来酰亚胺

HRID 55440

反应方程式

HRID 55440 反应方程式
[O-]CC.[Na+].[Cl:5][C:6]1[C:7]([O:9][C:10](=O)[C:11]=1[Cl:12])=[O:8].Cl.[CH3:15][NH2:16].O>C(O)(=O)C>[Cl:5][C:6]1[C:7]([N:16]([CH3:15])[C:10](=[O:9])[C:11]=1[Cl:12])=[O:8]

参与物

6

反应物 4

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]HCID 707282,3-二氯马来酸酐HCID 2723922乙醇钠HCID 6364545甲胺盐酸盐

产物 1

HCID 142932,3-二氯-N-甲基马来酰亚胺收率 64%

试剂、催化剂与溶剂 1

HCID 176醋酸溶剂

反应条件

温度
25 °C

实验过程

Sodium ethoxide (3.56 g, 50 mmol) was added to a solution containing 2,3-dichloromaleic anhydride (5.56 g, 33.3 mmol) and methylamine hydrochloride (3.50 g, 55.0 mmol) in 40 mL of acetic acid. The mixture was stirred under a CaCl2 drying tube at 25° C. for 16 hours and then refluxed for 4 hours. The cooled mixture was poured into water (350 mL) and extracted with EtOAc (3×75 mL). The combined organic extracts were washed with 100 mL portions of saturated aqueous NaHCO3, water and brine and dried (MgSO4). The solvent was evaporated under reduced pressure. The residue was recrystallized from ethanol to give 3.82 g (64%) of 2,3-dichloro N-methylmaleimide as white crystals. Concentration of the mother liquor and chromatography of the residue by radial preparative layer chromatography (Chromatotron, Harrison Research), gave an additional 0.81 g of 2,3-dichloro N-methylmaleimide, raising the yield to 77%.

后处理

  1. temperaturerefluxed for 4 hours
  2. extractionextracted with EtOAc (3×75 mL)
  3. washThe combined organic extracts were washed with 100 mL portions of saturated aqueous NaHCO3, water and brine
  4. dry with materialdried (MgSO4)
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was recrystallized from ethanol

来源与证据

ORD记录
ord-99833c5bcc6344e491e257e1a04e0a76
来源数据集
uspto-grants-1997_04
专利号
US05624949

关联笔记

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