반응 #4875

반응 방정식

sodium amide

1-methyl-3-pyrrolidinol

sodium methoxide

salicylamide

o-toluenesulfonylchloride

→

2-(1-Methyl-3-pyrrolidinyloxy)benzamide

용매

toluene

dimethylformamide

반응 조건

후처리

1. 1
   기타a temperature of 50° C
2. 2
   온도The mixture was cooled
3. 3
   온도while maintaining a temperature of 20°-30° C. with an ice bath
4. 4
   세척washed with water
5. 5
   건조The toluene solution was dried with sodium sulfate
6. 6
   농축concentrated
7. 7
   workup.DISSOLUTIONThe residue, dissolved in 500 ml of dimethylformamide
8. 8
   workup.ADDITIONwas added to a reaction mixture
9. 9
   기타prepared
10. 10
    기타the mixture was worked up as in preparation 1

실험 절차

To 85.6 g (2.2 moles) of sodium amide in 1.5 liter of dry toluene was added 202 g (2 moles) of 1-methyl-3-pyrrolidinol so as not to exceed a temperature of 50° C. The mixture was then heated to 70° C. for 4.5 hours. The mixture was cooled and 381 g (2 moles) of o-toluenesulfonylchloride was added at a rapid drop while maintaining a temperature of 20°-30° C. with an ice bath. The mixture was stirred at room temperature for 2.5 hours and washed with water. The toluene solution was dried with sodium sulfate and concentrated. The residue, dissolved in 500 ml of dimethylformamide, was added to a reaction mixture prepared by adding 119 g (2.2 moles) of sodium methoxide and 274 g (2.0 moles) of salicylamide to one liter of dimethylformamide and the mixture was worked up as in preparation 1. Yield of product was 170 g (38%), m.p. 116°-118° C.

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