Reacción #2045018

ord-4d0e68b9a7924dffa769b09b79c684ed

Ecuación de reacción

COC(=O)COc1ccc(N=C=O)cc1
(4-Isocyanato-phenoxy)-acetic acid methyl ester
OCCO
ethylene glycol
COC(=O)COc1ccc(NC(=O)OCCO)cc1
29
Rendimiento 82.9%
COC(=O)COc1ccc(NC(=O)OCCO)cc1
[4-(2-Hydroxy-ethoxycarbonylamino)-phenoxy]-acetic acid methyl ester
Rendimiento 82.9%

Disolventes

Condiciones de reacción

Temperatura
42°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Filtracióncrude 29 was filtered
  2. 2
    Otrodried
  3. 3
    Otropurified by column chromatography on silica gel

Procedimiento

(4-Isocyanato-phenoxy)-acetic acid methyl ester 28 (15 g, 72.46 mmol) was added to ethylene glycol (30 ml) at room temperature. The reaction was exothermic and the temperature raised to 42° C. Later the reaction mixture was stirred at room temperature for 16 hours. Water (100 ml) was added and crude 29 was filtered, dried and purified by column chromatography on silica gel using chloroform as eluant to get pure 29 (16.17 g, 82.9%) as a off-white powder. M.p: 85.5-87.5° C.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08409559B2uspto-grants-2013_04