三乙胺 → HCID 692365，化合物

HRID 2086561

反应方程式

HRID 2086561 反应方程式
[N+:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)/[CH:7]=[CH:8]/[C:9]([OH:11])=O)([O-:3])=[O:2].[C:15]([O:24][CH3:25])(=[O:23])[C:16]1[C:17](=[CH:19][CH:20]=[CH:21][CH:22]=1)[NH2:18].C(N(CC)CC)C>S(Cl)(Cl)=O.CN(C)C=O.O1CCOCC1>[CH3:25][O:24][C:15]([C:16]1[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=1[NH:18][C:9](=[O:11])/[CH:8]=[CH:7]/[C:6]1[CH:12]=[CH:13][CH:14]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)=[O:23]

参与物

7

反应物 3

HCID 8471三乙胺HCID 8635邻氨基苯甲酸甲酯HCID 687126对硝基苯乙烯酸(对硝基肉桂酸)

产物 1

HCID 692365HCID 692365，化合物

试剂、催化剂与溶剂 3

HCID 6228N,N-二甲基甲酰胺催化剂HCID 24386氯化亚砜溶剂HCID 312751,4-二氧六环溶剂

实验过程

965 mg (5.0 mmol) of trans-3-nitrocinnamic acid are refluxed for 20 minutes in 3 ml of thionyl chloride after the addition of one drop of dimethylformamide. Then the mixture is evaporated to dryness in vacuo and the resulting acid chloride is dissolved in 10 ml of dioxane. This solution is slowly added dropwise, with stirring, at ambient temperature, to a solution of 756 mg (5.0 mmol) of methyl anthranilate and 1.5 ml of triethylamine in 10 ml of dioxane. After one hour the solvent is evaporated off in vacuo, the residue is stirred into about 10 ml of water, then filtered off and the resulting crude product is purified by column chromatography over silica gel (eluant: dichloromethane/petroleum ether=2:1).

后处理

  1. customThen the mixture is evaporated to dryness in vacuo
  2. dissolutionthe resulting acid chloride is dissolved in 10 ml of dioxane
  3. additionThis solution is slowly added dropwise
  4. customAfter one hour the solvent is evaporated off in vacuo
  5. filtrationfiltered off
  6. customthe resulting crude product is purified by column chromatography over silica gel (eluant: dichloromethane/petroleum ether=2:1)

来源与证据

ORD记录
ord-7f791fbf7d284f2b817dbf6910f49c51
来源数据集
uspto-grants-2004_04
专利号
US06727250B2

关联笔记

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