反応 #54669

反応方程式

cyanogen chloride

aniline

triethylene diamine

benzenesulfonyl chloride

→

N-benzene sulfonyl phenyl cyanamide

収率 84.7%

溶媒

tetrahydrofuran

THF

tetrahydrofuran

反応条件

後処理

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

実験手順

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.

出典