Reacción #6585

Ecuación de reacción

3,4,5-trimethoxybenzoyl chloride

N,O-dimethylhydroxylamine hydrochloride

pyridine

→

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

Rendimiento 97.9%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroevaporate the solvent in vacuo
2. 2
   OtroPartition the residue between aqueous sodium chloride
3. 3
   workup.ADDITIONa 1:1 mixture of ethyl ether and methylene chloride
4. 4
   OtroSeparate the organic phase
5. 5
   Secadodry (Na2SO4)
6. 6
   Otroevaporate the solvent in vacuo
7. 7
   Otroto yield an oil
8. 8
   FiltraciónFilter the oil through silica gel eluting with 65% ethyl acetate/hexane

Procedimiento

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.

Fuente