Reaktion #1844684

Reaktionsgleichung

3,4,5-trimethoxybenzoyl chloride

N,O-dimethylhydroxylamine hydrochloride

pyridine

→

N-methoxy-N-methyl-(3,4,5-trimethoxy)benzamide

Ausbeute 97.9%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeevaporate the solvent in vacuo
2. 2
   SonstigePartition the residue between aqueous sodium chloride
3. 3
   workup.ADDITIONa 1:1 mixture of ethyl ether and methylene chloride
4. 4
   SonstigeSeparate the organic phase
5. 5
   Trocknendry (Na2SO4)
6. 6
   Sonstigeevaporate the solvent in vacuo
7. 7
   Sonstigeto yield an oil
8. 8
   FiltrationFilter the oil through silica gel eluting with 65% ethyl acetate/hexane

Vorschrift

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.

Quelle