Reaktion #54669

Reaktionsgleichung

cyanogen chloride

aniline

triethylene diamine

benzenesulfonyl chloride

→

N-benzene sulfonyl phenyl cyanamide

Ausbeute 84.7%

Lösungsmittel

tetrahydrofuran

THF

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeTo a 3 liter 3-necked flask equipped with a stirrer, addition funnel
2. 2
   Sonstigethermometer, and drying tube
3. 3
   Filtrationwas then filtered
4. 4
   workup.ADDITIONTo the filtrate was added 111 g of triethylene diamine
5. 5
   Temperaturwith cooling
6. 6
   workup.ADDITIONAfter this addition
7. 7
   Sonstigethe stirred reaction mixture
8. 8
   Sonstigeto return to room temperature over a 161
9. 9
   Sonstige2 hour period
10. 10
    FiltrationThe reaction mixture was filtered
11. 11
    workup.ADDITIONthe filament was added to water
12. 12
    Sonstigeto precipitate the product
13. 13
    SonstigeThe product was recrystallized from aqueous methanol

Vorschrift

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.

Quelle