4-Aminobenzonitrile → HCID 66561091, Verbindung
Reaktionsgleichung
[C:1]([C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1)#[N:2].[Cl:10][C:11]1[CH:16]=[C:15](Cl)[C:14]([N+:18]([O-:20])=[O:19])=[CH:13][C:12]=1[C:21]([F:24])([F:23])[F:22]>>[Cl:10][C:11]1[C:12]([C:21]([F:22])([F:23])[F:24])=[CH:13][C:14]([N+:18]([O-:20])=[O:19])=[C:15]([CH:16]=1)[NH:7][C:6]1[CH:8]=[CH:9][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1Komponenten
Versuchsvorschrift
4-cyano aniline (130 mg, 1.1 mmol) and 2,4-dichloro-5-nitrobenzotrifluoride (260 mg, 1 mmol) were used as starting materials. A general synthetic method of intermediate I was employed to get 5-chloro-N-(4-cyanophenyl)-2-nitro-4-trifluoromethylaniline (I-1) (281 mg) with a yield of 82%, as a yellow solid, and with a melting point of 180-182° C.; MS m/z (%) 359.2 (M+NH4, 100). I-1 and 4″-formyl-2″,6″-dimethylphenol were coupled by Method A in Preparation Example 2. The product was dissolved in 15 mL of THF, and was reacted with (EtO)2P(O)CH2CN (1.5 mmol) and an equivalent mole of potassium t-butoxide in THF by Method C in Preparation Example 2 under stirring for about 3 h. The product obtained by conventional post-treatment was isolated and purified through medium pressure column (dichloromethane/methanol) to get Compound 1, with a melting point of 248-250° C. and a yield of 87%. 1H NMR δ ppm 2.15 (6H, s, 2×CH3), 5.85 (1H, d, J=16.4 Hz, ═CH), 6.27 (1H, s, ArH-6), 7.10 (2H, d, J=8.8 Hz, ArH-2′,6′), 7.21 (2H, s, ArH-3″,5″), 7.32 (1H, d, J=16.4 Hz, CH═), 7.52 (2H, d, J=8.8 Hz, ArH-3′,5′), 8.67 (1H, s, ArH-3), 9.91 (1H, s, NH); MS m/z (%) 501.1 (M+Na, 100).
Quellen und Nachweise
- ORD-Eintrag
- ord-ee8a4b2107eb4ead983edc3369f067a7
- Quelldatensatz
- uspto-grants-2016_05
- Patentnummer
- US09340492B2
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