Reacción #2045024

Ecuación de reacción

6-(4-amino-phenoxy)hexanoic acid methyl ester

6-(4-Amino-phenoxy)-hexanoic acid methyl ester

triethylamine

triphosgene

→

36

Rendimiento 72.3%

6-(4-Isocyanato-phenoxy)-hexanoic acid methyl ester

Rendimiento 72.3%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrorose to 60° C
2. 2
   Temperaturamaintained at this temperature for 26 hours
3. 3
   TemperaturaThe reaction mixture was cooled to room temperature
4. 4
   Filtraciónthe solids were filtered
5. 5
   workup.DISTILLATIONthe toluene was distilled off under vacuum
6. 6
   Otroto get crude 36, which
7. 7
   workup.DISTILLATIONdistilled

Procedimiento

To a mixture of 6-(4-amino-phenoxy)hexanoic acid methyl ester 21 (26 grams, 109.7 mmol) and triethylamine (29.2 g, 288.56 mmol) in toluene (390 ml) under nitrogen atm. was added triphosgene (15.6 grams, 52.56 mmol) in one lot. The reaction was exothermic and the internal temperature rose to 60° C. Later, the reaction mixture was heated to 75° C. over a period of one hour and maintained at this temperature for 26 hours. The reaction mixture was cooled to room temperature, the solids were filtered, and the toluene was distilled off under vacuum to get crude 36, which was vacuum distilled to get pure 36 (10 g, 34.7%). M.p: 47-50° C.

Fuente