Triethylamine → 2-{4-[3-(3,4-Dichlorophenyl)propyl]phenylamino}-4-methoxy-5-nitrobenzoic acid methyl ester

HRID 488499Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 488499
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:19][O:20][C:21](=[O:34])[C:22]1[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[C:25]([O:31][CH3:32])=[CH:24][C:23]=1F.CCN(CC)CC>CC#N.C(Cl)Cl>[CH3:19][O:20][C:21](=[O:34])[C:22]1[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[C:25]([O:31][CH3:32])=[CH:24][C:23]=1[NH:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][CH2:10][CH2:9][C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)=[CH:17][CH:16]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 222697484-[3-(3,4-Dichloro-phenyl)propyl]phenylamineHCID 23404649Methyl 2-fluoro-4-methoxy-5-nitrobenzoate

Produkt 1

HCID 544753542-{4-[3-(3,4-Dichlorophenyl)propyl]phenylamino}-4-methoxy-5-nitrobenzoic acid methyl esterAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 4-[3-(3,4-dichloro-phenyl)propyl]phenylamine (0.94 g, 3.3 mmol), 2-fluoro-4-methoxy-5-nitro-benzoic acid methyl ester (0.75 g, 3.3 mmol), and Et3N (0.46 mL) in CH3CN (30 mL) was heated to reflux for 120 hours. The reaction mixture was cooled to room temperature, diluted with CH2Cl2 and washed with saturated NaHCO3. The organic layer was dried (Na2SO4) and concentrated to give a solid. Recrystallization with MeOH yielded 0.67 g (1.37 mmol, 42%) of the desired product.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 120 hours
  3. washwashed with saturated NaHCO3
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated
  6. customto give a solid
  7. customRecrystallization with MeOH

Quellen und Nachweise

ORD-Eintrag
ord-e7c8b0ecbb034184bd65f760efa1b60e
Quelldatensatz
uspto-grants-2005_12
Patentnummer
US06972287B1

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