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

HRID 6489

반응식

HRID 6489 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b6c9f2f23d2345ee9bd3354a56c32325
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05248825

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