反応 #318760

反応方程式

N,N-Dimethyl-2-[N-(2-hydroxyethyl)aminosulfonyl]-6-nitrobenzamide

NaH

methyl p-toluenesulfonate

sodium

→

N,N-Dimethyl-2-[N-(2-hyroxyethyl)-N-methylaminosulfonyl]-6-nitrobenzamide

溶媒

DMF

DMF

n-butylchloride

DMF

EtOAc

反応条件

後処理

1. 1
   workup.WAITat 60° for 23 hours
2. 2
   その他the white solid which formed
3. 3
   ろ過was filtered off
4. 4
   洗浄This precipitate was washed with EtOAc (100 ml)
5. 5
   洗浄The combined EtOAc solutions were washed with a saturated aqueous NaCl solution
6. 6
   乾燥dried (Na2SO4)
7. 7
   ろ過filtered
8. 8
   濃縮concentrated under reduced pressure
9. 9
   その他Pure produced

実験手順

A solution of N,N-Dimethyl-2-[N-(2-hydroxyethyl)aminosulfonyl]-6-nitrobenzamide (3.97 g, 12.5 mmol) in dry DMF (40 ml) was added slowly to a stirred suspension of 50% NaH (0.60 g, 12.5 mmol) in dry DMF (10 ml) under N2 at 20-25°. After formation of the sodium salt was complete, a solution of methyl p-toluenesulfonate (2.40 g, 12.9 mmol) in DMF (4 ml) was added and the reaction mixture stirred at 20-25° for 20 hours and then at 60° for 23 hours. The orange solution was mixed with EtOAc (400 ml) and the white solid which formed was filtered off. This precipitate was washed with EtOAc (100 ml). The combined EtOAc solutions were washed with a saturated aqueous NaCl solution, dried (Na2SO4), filtered and concentrated under reduced pressure. Pure produced, mp 107-08°, 2.5 g (60%) was obtained by flash chromatography over silica gel and elution with a 65% n-butylchloride-35% acetonitrile solvent mixture.

出典