反応 #2437

反応方程式

NaN3

Et3N

ethyl chloroformate

3-(N-tert-butoxylcarbonyl-N-methylamino)benzoic acid

→

title compound

収率 78.5%

3-(N-tert-Butoxylcarbonyl-N-methylamino)phenyl isocyanate

収率 78.5%

溶媒

water

acetone

acetone

water

toluene

反応条件

後処理

1. 1
   workup.STIRRINGThe mixture was stirred at the same temperature for a further 1 h
2. 2
   洗浄The organic portion was washed with brine
3. 3
   温度refluxed for 2 h
4. 4
   その他evaporated
5. 5
   workup.DISTILLATIONThe residue was distilled (100°-105° C./0.9-1.0 mmHg)

実験手順

Et3N (3.71 g, 36.7 mmol) and a solution of ethyl chloroformate (4.31 g, 39.7 mmol) in acetone (10 ml) were successively added dropwise to a solution of 3-(N-tert-butoxylcarbonyl-N-methylamino)benzoic acid (8.0 g, 31.8 mmol) in acetone (64 ml) below 5° C. After stirring for 30 min, a solution of NaN3 (3.10 g, 47.7 mmol) in water (10 ml) was added to the solution below 5° C. The mixture was stirred at the same temperature for a further 1 h, then poured into toluene (80 ml) and water (160 ml). The organic portion was washed with brine, refluxed for 2 h and evaporated. The residue was distilled (100°-105° C./0.9-1.0 mmHg) to afford the title compound (6.2 g, 78%) as a yellow oil.

出典