反応 #1483034

反応方程式

tert-butyl 2-aminoethylcarbamate

Et3N

nicotinic acid

oxalyl chloride

→

tert-butyl 2-(nicotinamido)ethylcarbamate

収率 74.0%

溶媒

CH2Cl2

CH2Cl2

反応条件

後処理

1. 1
   workup.DISSOLUTIONhad dissolved
2. 2
   その他(1 h)
3. 3
   その他The resulting reaction mixture
4. 4
   温度was warmed to room temperature
5. 5
   workup.STIRRINGstirred for 2 h
6. 6
   洗浄It was then washed with brine
7. 7
   乾燥dried over Na2SO4
8. 8
   ろ過filtered
9. 9
   濃縮concentrated under reduced pressure
10. 10
    その他Purification by silica gel chromatography (CH2Cl2)

実験手順

In a typical run, nicotinic acid (2.0 g, 16.2 mmol) was taken up in CH2Cl2 (20 mL) along with oxalyl chloride (1.4 mL, 16.2 mmol). After a few drops of DMF were added, the reaction mixture was stirred at room temperature until all the solids had dissolved and all gas evolution had ceased (1 h). This freshly prepared solution of the acid chloride was added dropwise at 0° C. to a solution containing tert-butyl 2-aminoethylcarbamate (2.6 g, 16.2 mmol) and Et3N (3.4 mL, 24.2 mmol) in CH2Cl2 (200 mL). The resulting reaction mixture was warmed to room temperature and stirred for 2 h. It was then washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. Purification by silica gel chromatography (CH2Cl2) afforded tert-butyl 2-(nicotinamido)ethylcarbamate (3.1 g, 74%).

出典