Methyl acetoacetate → 3-Isopropenyl-4-nitro-2(3H)-benzimidazolone

HRID 266696

Reaktionsgleichung

Reaktionsgleichung von HRID 266696
[OH-:1].[K+].C(OC)(=O)[CH2:4][C:5]([CH3:7])=O.[NH2:11][C:12]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[CH:15][C:13]=1[NH2:14].O.[CH3:23]O>C1(C)C(C)=CC=CC=1>[C:5]([N:11]1[C:12]2[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[CH:15][C:13]=2[NH:14][C:23]1=[O:1])([CH3:7])=[CH2:4]

Komponenten

6

Edukt 4

HCID 7757Methyl acetoacetateHCID 14797Potassium HydroxideHCID 43595253-Nitro-1,2-phenylenediamineHCID 22242641Methanol--water (1/1)

Produkt 1

HCID 105368363-Isopropenyl-4-nitro-2(3H)-benzimidazolone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

0.3 ml of 47% potassium hydroxide and then 115 mmol of methyl acetoacetate are added to 100 mmol of 2-amino-3-nitroaniline in 50 ml of xylene brought to 120° C. The whole mixture is brought to reflux for 4 hours and the water/methanol mixture formed is removed by means of a Dean and Stark apparatus. 18 ml of 47% potassium hydroxide and 200 ml of water are then added. The aqueous phase is washed with xylene, brought to pH=6 with 12N hydrochloric acid and then extracted with ethyl acetate and the expected product is purified by chromatography on a silica column, using a dichloromethane/methanol (95/5) mixture as eluent.

Aufarbeitung

  1. custombrought to 120° C
  2. temperatureto reflux for 4 hours
  3. customis removed by means of a Dean and Stark apparatus
  4. addition18 ml of 47% potassium hydroxide and 200 ml of water are then added
  5. washThe aqueous phase is washed with xylene
  6. extractionextracted with ethyl acetate
  7. customthe expected product is purified by chromatography on a silica column

Quellen und Nachweise

ORD-Eintrag
ord-f50582cc8b924b648e0fe750673e8523
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05652246

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