反应 #353628

反应方程式

2-methoxy-N,N-diethylbenzamide

sodium acetate

hydroxylamine-O-sulfonic acid

tetramethyl-ethylenediamine

s-butyl lithium

→

2-aminosulfonyl-6-methoxy-N,N-diethylbenzamide

收率 49.2%

溶剂

THF

THF

hexane

反应条件

后处理

1. 1
   workup.ADDITIONTo the solution was added dropwise
2. 2
   温度while maintaining the temperature at -60° C. or below
3. 3
   其他sulfur dioxide then bubbled into the reaction mixture
4. 4
   其他the reaction temperature below -50° C.
5. 5
   workup.STIRRINGThe mixture was then stirred at ambient temperature for two hours
6. 6
   workup.ADDITIONdiluted with 450 ml of hexane
7. 7
   其他the solid material which had separated
8. 8
   其他was collected
9. 9
   workup.DISSOLUTIONdissolved in 200 ml of water
10. 10
    workup.ADDITIONwas added in portions
11. 11
    workup.STIRRINGwith stirring
12. 12
    其他The white solid which separated
13. 13
    其他was collected
14. 14
    其他dried

实验过程

To a solution of 8.0 ml (0.053 mol) of tetramethyl-ethylenediamine (TMEDA) in 350 ml of THF at -70° C. was added 42 ml (0.055 mol) of a 1.3M solution of s-butyl lithium in hexane and the mixture was stirred for fifteen minutes. To the solution was added dropwise with stirring a solution of 10.36 g (0.050 mol) of 2-methoxy-N,N-diethylbenzamide in 150 ml of THF while maintaining the temperature at -60° C. or below and sulfur dioxide then bubbled into the reaction mixture, keeping the reaction temperature below -50° C. until the reaction mixture was acid to wet litmus paper. The mixture was then stirred at ambient temperature for two hours, diluted with 450 ml of hexane, and the solid material which had separated was collected, dissolved in 200 ml of water and the mixture treated with 65 g of sodium acetate, and 21.5 g (0.19 mol) of hydroxylamine-O-sulfonic acid was added in portions with stirring. The white solid which separated was collected and dried to give 7.04 g (49%) of 2-aminosulfonyl-6-methoxy-N,N-diethylbenzamide, mp 190°-194.5° C.

来源