Water → 2,6-Dimethyl-4-[3-(methylamino)-4-nitrophenoxy]aniline

HRID 1160836

Reaktionsgleichung

Reaktionsgleichung von HRID 1160836
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([NH:8][CH3:9])[CH:7]=1.[NH2:13][C:14]1[C:19]([CH3:20])=[CH:18][C:17]([OH:21])=[CH:16][C:15]=1[CH3:22].CC(C)([O-])C.[K+].O>CN(C)C(=O)C.C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C>[NH2:13][C:14]1[C:19]([CH3:20])=[CH:18][C:17]([O:21][C:2]2[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([NH:8][CH3:9])[CH:7]=2)=[CH:16][C:15]=1[CH3:22]

Komponenten

7

Edukt 4

HCID 962Water2×HCID 765434-Amino-3,5-dimethylphenolHCID 2580415-chloro-N-methyl-2-nitroanilineHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 667016652,6-Dimethyl-4-[3-(methylamino)-4-nitrophenoxy]anilineAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 314042,6-Di-tert-butyl-4-methylphenolKatalysatorHCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

To a solution of N-(5-chloro-2-nitrophenyl)-N-methylamine (8.00 g) in N,N-dimethylacetamide (112 ml) was added 2,6-di-t-butyl-4-methylphenol (0.24 g). Furthermore, to the resulting mixture were added 4-amino-3,5-dimethylphenol (6.47 g) and potassium t-butoxide (5.29 g) with stirring, and the resulting mixture was stirred at 60° C. for 30 minutes. After stirring, water (4 ml) was added to the reaction mixture, and furthermore water (120 ml) was added dropwise over a 2-hour interval, and then the resulting mixture was cooled gradually to room temperature. The crystalline solid precipitated was collected by filtration, washed with water (80 ml) and dried in vacuo to afford the title compound (11.45 g, yield: 93%) as a yellow crystalline solid.

Aufarbeitung

  1. stirringthe resulting mixture was stirred at 60° C. for 30 minutes
  2. stirringAfter stirring
  3. additionwas added dropwise over a 2-hour interval
  4. customThe crystalline solid precipitated
  5. filtrationwas collected by filtration
  6. washwashed with water (80 ml)
  7. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7af7d881506b4340ae6ccfe9b571051e
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07816552B2

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