3-(Trifluoromethyl)aniline → 4-(3'-Trifluoromethyl-4'-nitrophenyl)azobenzeneamine

HRID 399094

Reaktionsgleichung

Reaktionsgleichung von HRID 399094
FC(F)(F)[C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[NH2:12].[N:15]([O-:17])=[O:16].[Na+].[F:19][C:20]([F:29])([F:28])[C:21]1[CH:22]=[C:23]([NH2:27])[CH:24]=[CH:25][CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>Cl>[F:19][C:20]([F:28])([F:29])[C:21]1[CH:22]=[C:23]([N:27]=[N:9][C:7]2[CH:8]=[CH:3][C:4]([NH2:12])=[CH:5][CH:6]=2)[CH:24]=[CH:25][C:26]=1[N+:15]([O-:17])=[O:16]

Komponenten

6

Edukt 4

HCID 73753-(Trifluoromethyl)anilineHCID 11430Potassium CarbonateHCID 671284-Nitro-alpha,alpha,alpha-trifluoro-o-toluidineHCID 23668193Sodium Nitrite

Produkt 1

HCID 538591704-(3'-Trifluoromethyl-4'-nitrophenyl)azobenzeneamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel2×

Versuchsvorschrift

2-Trifluoromethyl-4-nitro-benzeneamine (4.92 g, 23.8 mmol) slurried in 5N hydrochloric acid (15.8 mL) and ice (16 g) was diazotized with 2M sodium nitrite (12.6 mL, 25 mmol) at 0°-5° C., followed by coupling with 3-trifluoromethylbenzeneamine (5.0 g, 31 mmol) in 5N hydrochloric acid (8 mL) at 0°-5° C. The mixture was stirred occasionally for 0.5 h, basified with 25 wt % aqueous potassium carbonate. The resulting solid was recrystallized from THF-ethanol (1:1) to give 4-(3'-trifluoromethyl-4'-nitrophenyl)azobenzeneamine: 1.8 g; mp 144.0°-145.5° C.

Aufarbeitung

  1. customThe resulting solid was recrystallized from THF-ethanol (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-1124fd87b5d34c729dbbbac4f5da0f1f
Quelldatensatz
uspto-grants-1998_10
Patentnummer
US05817743

Verknüpfte Notizen

Wird geladen…