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

HRID 37312

Reaktionsgleichung

Reaktionsgleichung von HRID 37312
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].N([O-])=O.[Na+].Cl[CH2:16][CH:17]([OH:31])[CH2:18][N:19]([CH2:26][CH:27]([OH:30])[CH2:28]Cl)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[NH3:32].[OH-].[Na+]>Cl.O>[CH2:18]([N:19]([C:20]1[CH:25]=[CH:24][C:23]([N:32]=[N:8][C:7]2[CH:9]=[CH:10][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[CH:22][CH:21]=1)[CH2:26][CH:27]1[O:30][CH2:28]1)[CH:17]1[O:31][CH2:16]1

Komponenten

8

Edukt 5

HCID 222AmmoniaHCID 74754-NitroanilineHCID 14798Sodium HydroxideHCID 134794141,1'-(Phenylimino)bis[3-chloro-2-propanol]HCID 23668193Sodium Nitrite

Produkt 1

HCID 217005194-(N,N-Diglycidylamino)-4'-nitroazobenzeneAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. filtrationThe diazonium salt solution is filtered
  2. customThe suspension obtained
  3. additionare then added drop by drop
  4. stirringstirring
  5. customfor 1 h
  6. washwashed until neutral
  7. dry with materialThe crude product is then dried
  8. customchromatographed on silica gel with dichloromethane/tetrahydrofuran as elution agent (yield: 34%)

Quellen und Nachweise

ORD-Eintrag
ord-bdae0a84e29d461fb55eb7698802efc4
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05420172

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