Triethylamine → 2-{4-[4-(3,4-Dichloro-phenyl)-butyl]-phenylamino}-5-nitro-benzoic acid

HRID 488507Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 488507
F[C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Cl:14][C:15]1[CH:16]=[C:17]([CH2:22][CH2:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=2)[CH:18]=[CH:19][C:20]=1[Cl:21].CCN(CC)CC>C(#N)C>[Cl:14][C:15]1[CH:16]=[C:17]([CH2:22][CH2:23][CH2:24][CH2:25][C:26]2[CH:27]=[CH:28][C:29]([NH:32][C:2]3[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=3[C:4]([OH:6])=[O:5])=[CH:30][CH:31]=2)[CH:18]=[CH:19][C:20]=1[Cl:21]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 2809972-Fluoro-5-nitrobenzoic acidHCID 136560814-[4-(3,4-Dichlorophenyl)butyl]phenylamine

Produkt 1

HCID 222698092-{4-[4-(3,4-Dichloro-phenyl)-butyl]-phenylamino}-5-nitro-benzoic acidAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 2-fluoro-5-nitrobenzoic acid (1.85 g, 0.01 mol), 4-[4-(3,4-dichlorophenyl)butyl]-phenylamine (2.94 g, 0.01 mol) and Et3N (2.80 mL) in acetonitrile (110 mL) was heated to reflux for 48 hours. The reaction mixture was cooled and concentrated in vacuo to remove the solvent. The residue was dissolved in CH2C2 and washed with diluted HCl. The organic layer was dried Na2SO4), concentrated in vacuo to give a crude solid. Purification by flash chromatography (silica gel, CH2Cl2) yielded 1.40 g (0.003 mol, 30%) of the desired product.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 48 hours
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated in vacuo
  5. customto remove the solvent
  6. dissolutionThe residue was dissolved in CH2C2
  7. washwashed with diluted HCl
  8. concentrationconcentrated in vacuo
  9. customto give a crude solid
  10. customPurification by flash chromatography (silica gel, CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-dfcd1b1382264f4f813127a9b6ca8e7f
Quelldatensatz
uspto-grants-2005_12
Patentnummer
US06972287B1

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