Reaction #95993

Reaction equation

4-amino-1-hydroxy-N,N-dioctadecyl-2-naphthamide

4-(2-cyanoethylsulfonyl)benzenesulfonyl chloride

→

tan solid

Yield 62.0%

4-[4-(2-cyanoethylsulfonyl)benzenesulfonamido]-1-hydroxy-N,N-dioctadecyl-2-naphthamide

Yield 62.0%

Solvents

—

ice

pyridine

Conditions

Workup

1. 1
   Temperaturewas warmed to 20° to 25° C.
2. 2
   workup.WAITheld for one hour
3. 3
   Filtrationwater, filtered
4. 4
   Otherdried
5. 5
   OtherThe product was recrystallized from hexane

Procedure

A solution of 4-amino-1-hydroxy-N,N-dioctadecyl-2-naphthamide (U.S. Pat. No. 4,135,929) (0.03 mol) in 450 ml of degassed pyridine was cooled to 5° to 10° C. and 8.8 g (0.03 mol) of 4-(2-cyanoethylsulfonyl)benzenesulfonyl chloride was added scoopwise at 0° to 5° C. The mixture was stirred for one hour at this temperature and was warmed to 20° to 25° C. and held for one hour. The reaction mixture was drowned in 2 liters of ice and water, filtered, reslurried in water and dried. The product was recrystallized from hexane to give 18 g (62 percent) of a tan solid, melting point 85° to 86° C.

Source