تفاعل #318760

معادلة التفاعل

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

المذيبات

DMF

DMF

n-butylchloride

DMF

EtOAc

ظروف التفاعل

المعالجة

1. 1
   workup.WAITat 60° for 23 hours
2. 2
   أخرىthe white solid which formed
3. 3
   ترشيحwas filtered off
4. 4
   غسيلThis precipitate was washed with EtOAc (100 ml)
5. 5
   غسيلThe combined EtOAc solutions were washed with a saturated aqueous NaCl solution
6. 6
   تجفيفdried (Na2SO4)
7. 7
   ترشيحfiltered
8. 8
   تركيزconcentrated under reduced pressure
9. 9
   أخرىPure produced

الإجراء التجريبي

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.

المصدر