Reacción #54669

Ecuación de reacción

cyanogen chloride

aniline

triethylene diamine

benzenesulfonyl chloride

→

N-benzene sulfonyl phenyl cyanamide

Rendimiento 84.7%

Disolventes

tetrahydrofuran

THF

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroTo a 3 liter 3-necked flask equipped with a stirrer, addition funnel
2. 2
   Otrothermometer, and drying tube
3. 3
   Filtraciónwas then filtered
4. 4
   workup.ADDITIONTo the filtrate was added 111 g of triethylene diamine
5. 5
   Temperaturawith cooling
6. 6
   workup.ADDITIONAfter this addition
7. 7
   Otrothe stirred reaction mixture
8. 8
   Otroto return to room temperature over a 161
9. 9
   Otro2 hour period
10. 10
    FiltraciónThe reaction mixture was filtered
11. 11
    workup.ADDITIONthe filament was added to water
12. 12
    Otroto precipitate the product
13. 13
    OtroThe product was recrystallized from aqueous methanol

Procedimiento

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.

Fuente