Reaktion #65590

Reaktionsgleichung

ammonia

sodium nitrite

4-nitroaniline

N,N-bis(3-chloro-2-hydroxypropyl)-aniline

caustic soda

→

4-(N,N-Diglycidylamino)-4'-nitroazobenzene

Ausbeute 34.0%

Lösungsmittel

water

hydrochloric acid

hydrochloric acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe diazonium salt solution is filtered
2. 2
   SonstigeThe suspension obtained
3. 3
   workup.ADDITIONare then added drop by drop
4. 4
   workup.STIRRINGstirring
5. 5
   Sonstigefor 1 h
6. 6
   Waschenwashed until neutral
7. 7
   TrocknenThe crude product is then dried
8. 8
   Sonstigechromatographed on silica gel with dichloromethane/tetrahydrofuran as elution agent (yield: 34%)

Vorschrift

0.25 mol of 4-nitroaniline are stirred in 150 ml of 16% aqueous hydrochloric acid and diazotized at 0° to 5° C. with 0.25 mol of sodium nitrite in 100 ml of water. The diazonium salt solution is filtered, added drop by drop to a solution of 0.25 mol N,N-bis(3-chloro-2-hydroxypropyl)-aniline in 250 ml 5% aqueous hydrochloric acid at 5° to 10° C. and stirred 1 h. The suspension obtained is neutralized with 25% aqueous ammonia solution, 1000 ml of 50% aqueous caustic soda solution are then added drop by drop and stirring takes place for 1 h. The precipitate is drawn off and washed until neutral. The crude product is then dried and chromatographed on silica gel with dichloromethane/tetrahydrofuran as elution agent (yield: 34%); MP: 135°-136° C.

Quelle