Реакция #4875

Уравнение реакции

sodium amide

1-methyl-3-pyrrolidinol

sodium methoxide

salicylamide

o-toluenesulfonylchloride

→

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

Растворители

toluene

dimethylformamide

Условия реакции

Обработка

1. 1
   Другоеa temperature of 50° C
2. 2
   ТемператураThe mixture was cooled
3. 3
   Температураwhile maintaining a temperature of 20°-30° C. with an ice bath
4. 4
   Промывкаwashed with water
5. 5
   СушкаThe toluene solution was dried with sodium sulfate
6. 6
   Концентрированиеconcentrated
7. 7
   workup.DISSOLUTIONThe residue, dissolved in 500 ml of dimethylformamide
8. 8
   workup.ADDITIONwas added to a reaction mixture
9. 9
   Другоеprepared
10. 10
    Другоеthe mixture was worked up as in preparation 1

Методика

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.

Источник