Reaktion #3791

Reaktionsgleichung

2,2'-dithiobisbenzoyl chloride

4-(aminomethyl)benzenesulfonamide hydrochloride hydrate

N-methyl-N-(trimethylsilyl)acetamide

→

title compound

Ausbeute 35.4%

2,2'-Dithiobis[N-[[4-(aminosulfonyl)phenyl]methy]benzamide]

Ausbeute 35.4%

Lösungsmittel

pyridine

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe solution was cooled to 0° C. to 5° C.
2. 2
   Sonstigethe dichloromethane was removed in vacuo
3. 3
   SonstigeThe crude product was precipitated with the addition of water
4. 4
   Filtrationthe resulting solid was collected by filtration
5. 5
   SonstigeThe crude product was recrystallized from a mixture of dimethylformamide, ethanol, and water

Vorschrift

A slurry of 4-(aminomethyl)benzenesulfonamide hydrochloride hydrate (6.5 g, 29 mmol) in 100 mL pyridine was allowed to stir with N-methyl-N-(trimethylsilyl)acetamide (13.4 mL, 83.0 mmol) until a homogenous solution occurred. The solution was cooled to 0° C. to 5° C. and a solution of 2,2'-dithiobisbenzoyl chloride (4.0 9, 16.0 mmol) in 20 mL dichloromethane was added dropwise. The resulting solution was allowed to stir for 18 hours and the dichloromethane was removed in vacuo. The crude product was precipitated with the addition of water and the resulting solid was collected by filtration. The crude product was recrystallized from a mixture of dimethylformamide, ethanol, and water to yield 3.3 g of the title compound, mp 267°-269° C.

Quelle