吡啶 → N,3,4,5-四甲氧基-N-甲基-苯甲酰胺

HRID 6489

反应方程式

HRID 6489 反应方程式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[C:6](Cl)=[O:7].Cl.[CH3:17][NH:18][O:19][CH3:20].N1C=CC=CC=1>C(O)C>[CH3:20][O:19][N:18]([CH3:17])[C:6](=[O:7])[C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[CH:9]=1

参与物

5

反应物 3

HCID 1049吡啶HCID 782823,4,5-三甲氧基苯甲酰氯HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

产物 1

HCID 267535N,3,4,5-四甲氧基-N-甲基-苯甲酰胺收率 97.9%

试剂、催化剂与溶剂 1

HCID 702乙醇溶剂

反应条件

温度
0 °C

实验过程

Dissolve 3,4,5-trimethoxybenzoyl chloride (2.3 g, 10 mmol) and N,O-dimethylhydroxylamine hydrochloride (1.10 g, 11 mmol) in ethanol-free chloroform at room temperature. Cool the solution to 0° C. and add pyridine (1.85 g, 22 mmol). Stir at ambient temperature for 1 hour and evaporate the solvent in vacuo. Partition the residue between aqueous sodium chloride and a 1:1 mixture of ethyl ether and methylene chloride. Separate the organic phase, dry (Na2SO4), and evaporate the solvent in vacuo to yield an oil. Filter the oil through silica gel eluting with 65% ethyl acetate/hexane to yield 2.5 g of N-methoxy-N-methyl-(3,4,5-trimethoxy)benzamide.

后处理

  1. customevaporate the solvent in vacuo
  2. customPartition the residue between aqueous sodium chloride
  3. additiona 1:1 mixture of ethyl ether and methylene chloride
  4. customSeparate the organic phase
  5. dry with materialdry (Na2SO4)
  6. customevaporate the solvent in vacuo
  7. customto yield an oil
  8. filtrationFilter the oil through silica gel eluting with 65% ethyl acetate/hexane

来源与证据

ORD记录
ord-b6c9f2f23d2345ee9bd3354a56c32325
来源数据集
uspto-grants-1993_09
专利号
US05248825

关联笔记

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