Reacción #1869212

ord-ef69b6f7495e473da852aa96bc95b40c

Ecuación de reacción

CCOC(C)=O
ethyl acetate
COc1ccc(CC(=O)O)c(OC)c1
(2,4-dimethoxyphenyl)acetic acid
O=C(n1ccnc1)n1ccnc1
N,N-carbonyldiimidazole
CN
methyl amine
CNC(=O)Cc1ccc(OC)cc1OC
subtitled compound
Rendimiento 73.3%
CNC(=O)Cc1ccc(OC)cc1OC
2-(2,4-Dimethoxyphenyl)-N-methylacetamide
Rendimiento 73.3%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.STIRRINGthe reaction mixture was stirred at room temperature over the week-end
  2. 2
    SecadoThe organic layer was dried over Na2SO4
  3. 3
    Filtraciónfiltered
  4. 4
    Concentraciónconcentrated
  5. 5
    OtroThe residue was purified by silica gel flash chromatography (0-80% ethyl acetate in petroleum spirit)

Procedimiento

A mixture of (2,4-dimethoxyphenyl)acetic acid (577 mg, 3.0 mmol) and N,N-carbonyldiimidazole (608 mg, 3.75 mmol) in DMF (10 mL) was stirred at room temperature for 45 min, aqueous 40% methyl amine (4.5 mL) was added and the reaction mixture was stirred at room temperature over the week-end. The reaction mixture was is partitoned between ethyl acetate and H2O. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel flash chromatography (0-80% ethyl acetate in petroleum spirit) to give the subtitled compound (460 mg).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07498338B2uspto-grants-2009_03