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p-Aminoacetophenone → N-[4-(1-hydroxyiminoethyl)phenyl]-N'-bis(methoxycarbonyl)methylurea

HRID 247226
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 247226
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1)=O.[N:11]([CH:14]([C:19]([O:21][CH3:22])=[O:20])[C:15]([O:17][CH3:18])=[O:16])=[C:12]=[O:13].Cl.[NH2:24][OH:25].C(OC)(OC)OC>C1COCC1.N1C=CC=CC=1>[OH:25][N:24]=[C:2]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:12]([NH:11][CH:14]([C:19]([O:21][CH3:22])=[O:20])[C:15]([O:17][CH3:18])=[O:16])=[O:13])=[CH:6][CH:5]=1)[CH3:1]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 7468p-AminoacetophenoneHCID 9005Trimethyl orthoformateHCID 443297Hydroxyamine hydrochlorideHCID 14876291Dimethyl isocyanatomalonate

Produkt 1

HCID 86741886N-[4-(1-hydroxyiminoethyl)phenyl]-N'-bis(methoxycarbonyl)methylurea

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049
Pyridine
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 0.02 mol 4-aminoacetophenone in 40 mL THF if added dropwise to a solution of 0.02 mol of dimethyl isocyanatomalonate and 5 mL pyridine in 40 mL THF, and the reaction mixture is stirred for 3 hours. The solvent is then removed by rotary evaporator. The residue is dispersed in 50 mL CH3OH, and 0.022 hydroxylamine hydrochloride and 0.06 mol trimethyl orthoformate are added. The reaction mixture is heated to reflux for 10 hours. The solvent is removed by rotary evaporator. Addition of water to the residue results in formation of N-[4-(1-hydroxyiminoethyl)phenyl]-N'-bis(methoxycarbonyl)methylurea, which is then treated with NaOCH3 to adjust the pH to 10. The solution is heated to reflux for 2.5 hours, and the solvent is removed under vacuum. The residue is washed with cold water to yield the crude 3-[4-(1-hydroxyiminoethyl)phenyl]-5-methoxycarbonylhydantoin.

Aufarbeitung

  1. customThe solvent is then removed by rotary evaporator
  2. additionThe residue is dispersed in 50 mL CH3OH
  3. temperatureThe reaction mixture is heated
  4. temperatureto reflux for 10 hours
  5. customThe solvent is removed by rotary evaporator
  6. additionAddition of water to the residue

Quellen und Nachweise

ORD-Eintrag
ord-adcab2c90b9d4fa39e7676b8a03f3d0f
Quelldatensatz
uspto-grants-1987_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04705864

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