4-(Trifluoromethyl)aniline → 2,5-bis(4-nitrophenyl)-1-(4-(trifluoromethyl)phenyl)-1H-pyrrole

HRID 1470961Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1470961
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=O)[CH2:11][CH2:12][C:13]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[F:25][C:26]([F:35])([F:34])[C:27]1[CH:33]=[CH:32][C:30]([NH2:31])=[CH:29][CH:28]=1>C(O)(=O)C.O.C(OCC)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:31]([C:30]3[CH:32]=[CH:33][C:27]([C:26]([F:25])([F:34])[F:35])=[CH:28][CH:29]=3)[C:13]([C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=3)=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Komponenten

6

Edukt 2

HCID 99644-(Trifluoromethyl)anilineHCID 137628911,4-Bis(4-nitrophenyl)butane-1,4-dione

Produkt 1

HCID 866491052,5-bis(4-nitrophenyl)-1-(4-(trifluoromethyl)phenyl)-1H-pyrroleAusbeute 8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

To a slurry of the product from Example 1A (1.00 g, 3.05 mmol) in acetic acid (30 mL) was added 4-(trifluoromethyl)aniline (1.9 mL, 15 mmol). The mixture was heated to 170° C. for 15 minutes under microwave irradiation. The cooled mixture was diluted with water and diethyl ether and stirred vigorously for 15 minutes and then filtered. The crude product was purified by chromatography on silica gel eluting with a solvent gradient of 0-30% ethyl acetate in hexane. Product containing fractions were combined and concentrated under reduced pressure and then triturated with diethyl ether to give the title compound (110 mg, 8% yield).

Aufarbeitung

  1. filtrationfiltered
  2. customThe crude product was purified by chromatography on silica gel eluting with a solvent gradient of 0-30% ethyl acetate in hexane
  3. additionProduct containing fractions
  4. concentrationconcentrated under reduced pressure
  5. customtriturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-32db2837d6aa46f99fcc2491a8e99a32
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006387B2

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