盐酸 → HCID 67436541，化合物

HRID 1663231笔记

反应方程式

HRID 1663231 反应方程式
Cl.[O:2]=[C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[N:4]1[CH2:13][CH2:14][C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=1.[CH2:23](N)[CH2:24][NH2:25]>C(O)C>[NH:20]1[CH2:23][CH2:24][N:25]=[C:19]1[C:18]1[CH:17]=[CH:16][C:15]([CH2:14][CH2:13][N:4]2[C:3](=[O:2])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]2=[O:12])=[CH:22][CH:21]=1

参与物

5

反应物 3

HCID 313盐酸HCID 3301乙二胺HCID 674369234-[2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]benzonitrile

产物 1

HCID 67436541HCID 67436541，化合物收率 62%

试剂、催化剂与溶剂 1

HCID 702乙醇溶剂

实验过程

Dry hydrogen chloride gas was bubbled through an ice cold solution of 4-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-benzonitrile (7.83 g, 28.3 mmol) in ethanol (400 mL) for 3 h, then the so obtained mixture was kept at 8° C. overnight. The reaction mixture was concentrated in vacuo, the residue was dissolved in dry ethanol (400 mL), ethylenediamine (2.0 mL, 29.7 mmol) was added and the reaction mixture was stirred at room temperature overnight. The mixture was concentrated in vacuo, the residue was partitioned between dichloromethane (400 mL) and concentrated ammonium hydroxide (400 mL), the phases were separated and the water phase was extracted with dichloromethane (2×200 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated. The crude product was recrystallized from 2-propanol to yield 5.58 g (62%) of the title compound as a white solid.

后处理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in dry ethanol (400 mL)
  3. concentrationThe mixture was concentrated in vacuo
  4. customthe residue was partitioned between dichloromethane (400 mL) and concentrated ammonium hydroxide (400 mL)
  5. customthe phases were separated
  6. extractionthe water phase was extracted with dichloromethane (2×200 mL)
  7. dry with materialThe combined organic layers were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was recrystallized from 2-propanol

来源与证据

ORD记录
ord-b77423716e3645508e69277aa65255f9
来源数据集
uspto-grants-2011_10
专利号
US08034827B2

反应笔记

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