Pyridine → N,3,4,5-tetramethoxy-N-methyl-Benzamide

HRID 6489

反応式

HRID 6489 の反応式
[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

参加物

5

反応物 3

HCID 1049PyridineHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

生成物 1

HCID 267535N,3,4,5-tetramethoxy-N-methyl-Benzamide収率 97.9%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b6c9f2f23d2345ee9bd3354a56c32325
出典データセット
uspto-grants-1993_09
特許番号
US05248825

関連ノート

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