Guanidine → 2-(4-Ethyl-7-methyl-benzo[b]thiophen-5-yloxy)-3-phenylamino-acrylonitrile

HRID 38429

反应方程式

HRID 38429 反应方程式
CN(C)[CH:3]([N:20]([CH3:22])C)[CH:4]([O:7][C:8]1[CH:16]=[C:15]([CH3:17])[C:11]2[S:12][CH:13]=[CH:14][C:10]=2[C:9]=1[CH2:18][CH3:19])[C:5]#[N:6].Cl.N[C:26]1[CH:31]=[CH:30]C=[CH:28][CH:27]=1.Cl.NC(N)=N.C[O-].[Na+].NC(N)=N>C(O)C>[CH2:18]([C:9]1[C:10]2[CH:14]=[CH:13][S:12][C:11]=2[C:15]([CH3:17])=[CH:16][C:8]=1[O:7][C:4](=[CH:3][NH:20][C:22]1[CH:30]=[CH:31][CH:26]=[CH:27][CH:28]=1)[C:5]#[N:6])[CH3:19]

参与物

7

反应物 5

HCID 3520GuanidineHCID 5742Guanidine HydrochlorideHCID 8870盐酸苯胺HCID 10942334甲醇钠HCID 595987063,3-Bis-dimethylamino-2-(4-ethyl-7-methyl-benzo[b]thiophen-5-yloxy)-propionitrile

产物 1

HCID 670534132-(4-Ethyl-7-methyl-benzo[b]thiophen-5-yloxy)-3-phenylamino-acrylonitrile收率 55%

试剂、催化剂与溶剂 1

HCID 702乙醇溶剂2 次

实验过程

3,3-Bis-dimethylamino-2-(4-ethyl-7-methyl-benzo[b]thiophen-5-yloxy)-propionitrile (590 mg, 2 mmol) and aniline HCl (1.1 g, 9 mmol) in 5 mL absolute ethanol were heated at reflux for 2.0 hours. In a separate flask, guanidine HCl (0.850 mg., 9 mmol) and sodium methoxide solution (1.83 ml, 9 mmol, 4.9 molar solution in methanol) were mixed in 1 ml Ethanol. The guanidine solution was added to the reaction mixture via pipette, and the reaction mixture was heated to reflux for 5 hours, then cooled. Solvent was removed in vacuo, and the residue was, chromatographed (5% MeOH/methylene chloride/1% Na4OH) to give 368 mg 2-(4-Ethyl-7-methyl-benzo[b]thiophen-5-yloxy)-3-phenylamino-acrylonitrile, 61%. Also present was 50 mg of 5-(4-Ethyl-7-methyl-benzo[b]thiophen-5-yloxy)-pyrimidine-2,4-diamine, 9%.

后处理

  1. temperatureat reflux for 2.0 hours
  2. temperaturethe reaction mixture was heated
  3. temperatureto reflux for 5 hours
  4. temperaturecooled
  5. customSolvent was removed in vacuo
  6. customchromatographed (5% MeOH/methylene chloride/1% Na4OH)

来源与证据

ORD记录
ord-cc4c99025821491089fd53ccd157da18
来源数据集
uspto-grants-2013_09
专利号
US08524725B2

关联笔记

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