Réaction #2045024

Équation de réaction

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

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

triethylamine

triphosgene

→

36

Rendement 72.3%

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

Rendement 72.3%

Solvants

toluene

Conditions de réaction

Traitement

1. 1
   Autrerose to 60° C
2. 2
   Températuremaintained at this temperature for 26 hours
3. 3
   TempératureThe reaction mixture was cooled to room temperature
4. 4
   Filtrationthe solids were filtered
5. 5
   workup.DISTILLATIONthe toluene was distilled off under vacuum
6. 6
   Autreto get crude 36, which
7. 7
   workup.DISTILLATIONdistilled

Mode opératoire

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.

Source