Formaldehyde → [2-[[3-(Dimethylamino)propyl](3-nitro-2-pyridinyl)amino]phenyl]phenylmethanone

HRID 463021

Reaktionsgleichung

Reaktionsgleichung von HRID 463021
[N+:1]([C:4]1[C:5]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:18])=[N:6][CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Cl.[CH3:26][N:27]([CH3:32])[CH2:28][CH2:29][CH2:30]Cl.[OH-].[Na+].C=O>[Cl-].C(C([NH3+])(C(=O)CCCCCCC)C(=O)CCCCCCC)(=O)CCCCCCC.C(Cl)Cl>[CH3:26][N:27]([CH3:32])[CH2:28][CH2:29][CH2:30][N:10]([C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=[CH:7][N:6]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:18]

Komponenten

7

Edukt 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 13388384{2-[(3-Nitropyridin-2-yl)amino]phenyl}(phenyl)methanone

Produkt 1

HCID 54525496[2-[[3-(Dimethylamino)propyl](3-nitro-2-pyridinyl)amino]phenyl]phenylmethanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 77620884Tricaprylylmethyl ammonium chlorideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture 2 g (0.006 mole) of [2-[(3-nitro-2-pyridinyl)amino]phenyl]phenylmethanone, 3 g (0.019 mole) of 3-dimethylaminopropyl chloride hydrochloride, 10 ml of 50% aqueous sodium hydroxide, 5 drops tricaprylylmethyl ammonium chloride (phase transfer catalyst) and 15 ml methylene chloride was stirred and maintained at reflux for 18 hrs. Chemical ionization mass spectral analysis indicated only a trace of the starting methanone was present with good conversion to the title compound. The reaction mixture was partially neutralized with 10% hydrochloric acid. The diluted but still basic mixture was extracted with methylene chloride and the methylene chloride layer evaporated to give 1.1 g brown residue predominantly the title compound.

Aufarbeitung

  1. temperaturemaintained
  2. temperatureat reflux for 18 hrs

Quellen und Nachweise

ORD-Eintrag
ord-2fa674b05ad344a5aebc1360cd166856
Quelldatensatz
uspto-grants-1985_05
Patentnummer
US04518603

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