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

HRID 6489

Reaktionsgleichung

Reaktionsgleichung von HRID 6489
[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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 267535N,3,4,5-tetramethoxy-N-methyl-BenzamideAusbeute 97,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-b6c9f2f23d2345ee9bd3354a56c32325
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05248825

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