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p-Aminoacetophenone → N-[4-(1-hydroxyiminoethyl)phenyl]-N'-ethoxycarbonylmethylurea

HRID 649677
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 649677
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1)=O.[N-:11]=[C:12]=[O:13].[CH2:14]([O:16][C:17](=[O:20])[CH2:18]N)[CH3:15].Cl.[NH2:22][OH:23].C(OC)(OC)OC>C1COCC1.N1C=CC=CC=1>[OH:23][N:22]=[C:2]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:12]([NH:11][CH2:18][C:17]([O:16][CH2:14][CH3:15])=[O:20])=[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 86647037Ethyl 2-aminoacetate isocyanate

Produkt 1

HCID 72742601N-[4-(1-hydroxyiminoethyl)phenyl]-N'-ethoxycarbonylmethylurea

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049
Pyridine
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 0.02 mol 4-aminoacetophenone in 40 mL THF is added dropwise to a solution of 0.02 mol of glycine ethyl ester isocyanate 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 mol 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 precipitation of N-[4-(1-hydroxyiminoethyl)phenyl]-N'-ethoxycarbonylmethylurea, which is isolated by filtration and dried.

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-86cc970264264d4a8369454102d5f91a
Quelldatensatz
uspto-grants-1988_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04740611

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