반응 #54669

반응 방정식

cyanogen chloride

aniline

triethylene diamine

benzenesulfonyl chloride

→

N-benzene sulfonyl phenyl cyanamide

수율 84.7%

용매

tetrahydrofuran

THF

tetrahydrofuran

반응 조건

후처리

1. 1
   기타To a 3 liter 3-necked flask equipped with a stirrer, addition funnel
2. 2
   기타thermometer, and drying tube
3. 3
   여과was then filtered
4. 4
   workup.ADDITIONTo the filtrate was added 111 g of triethylene diamine
5. 5
   온도with cooling
6. 6
   workup.ADDITIONAfter this addition
7. 7
   기타the stirred reaction mixture
8. 8
   기타to return to room temperature over a 161
9. 9
   기타2 hour period
10. 10
    여과The reaction mixture was filtered
11. 11
    workup.ADDITIONthe filament was added to water
12. 12
    기타to precipitate the product
13. 13
    기타The product was recrystallized from aqueous methanol

실험 절차

To a 3 liter 3-necked flask equipped with a stirrer, addition funnel, thermometer, and drying tube was charged 93.1 g (1.0 mole) of aniline, 111 g (1.1 moles) of triethylene diamine and 250 ml. of tetrahydrofuran. To this reaction mixture was added dropwise a solution of 176.6 g (1 mole) of benzenesulfonyl chloride in 300 ml. of tetrahydrofuran. The reaction mixture was stirred at room temperature for 2.5 hours and was then filtered. To the filtrate was added 111 g of triethylene diamine and this solution was added dropwise to a solution of 87 g (1.41 moles) of cyanogen chloride in 100 ml. of THF which was maintained at -5° C. with cooling. After this addition was complete the stirred reaction mixture was allowed to return to room temperature over a 161/2 hour period. The reaction mixture was filtered and the filament was added to water to precipitate the product. The product was recrystallized from aqueous methanol to yield 218 g (84.7%) of N-benzene sulfonyl phenyl cyanamide, m.p. 65°-66° C.

출처