4-Aminophenol → alpha-(1-Methyl-2-nitroimidazol-5-yl)-p-anisidine

HRID 462404

Reaktionsgleichung

Reaktionsgleichung von HRID 462404
[CH3:1][N:2]1[C:6]([CH2:7][OH:8])=[CH:5][N:4]=[C:3]1[N+:9]([O-:11])=[O:10].[NH2:12][C:13]1[CH:18]=[CH:17][C:16](O)=[CH:15][CH:14]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[CH3:1][N:2]1[C:6]([CH2:7][O:8][C:16]2[CH:17]=[CH:18][C:13]([NH2:12])=[CH:14][CH:15]=2)=[CH:5][N:4]=[C:3]1[N+:9]([O-:11])=[O:10]

Komponenten

6

Edukt 4

HCID 4034-AminophenolHCID 11776TriphenylphosphineHCID 702921-Methyl-2-nitro-1H-imidazole-5-methanolHCID 75555Diisopropyl diazene-1,2-dicarboxylate

Produkt 1

HCID 20398279alpha-(1-Methyl-2-nitroimidazol-5-yl)-p-anisidineAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A suspension of 30 g of 1-methyl-2-nitroimidazole-5-methanol, 22 g of 4-aminophenol and 55 g of triphenylphosphane in 600 ml of anhydrous tetrahydrofuran was treated dropwise with vigorous stirring within 20 minutes with a solution of 42.5 g of diisopropyl azodicarboxylate in 300 ml of anhydrous tetrahydrofuran. The mixture was maintained at a temperature of 20°-24° C. by external cooling. After 2 hours, the clear solution obtained was evaporated under reduced pressure and the residue was boiled briefly with a mixture of 125 ml of methylene chloride and 125 ml of ethyl acetate to yield 24.4 g (52%) of crystalline α-(1-methyl-2-nitroimidazol-5-yl)-p-anisidine, m.p. 168°-170° C.

Aufarbeitung

  1. additionwas treated dropwise
  2. temperatureThe mixture was maintained at a temperature of 20°-24° C. by external cooling
  3. customthe clear solution obtained
  4. customwas evaporated under reduced pressure
  5. additionthe residue was boiled briefly with a mixture of 125 ml of methylene chloride and 125 ml of ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-f4ee2f00f7c247ed9b6bf2bbcfec1c33
Quelldatensatz
uspto-grants-1985_05
Patentnummer
US04515790

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