p-Aminoacetophenone → HCID 86741882, Verbindung

HRID 649689Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 649689
[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].[CH3:14][O:15][C:16](=[O:24])[C@H:17]([CH2:19][S:20][C:21](=[O:23])[CH3:22])N.Cl.[NH2:26][OH:27].C(OC)(OC)OC>C1COCC1.N1C=CC=CC=1>[OH:27][N:26]=[C:2]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:12]([NH:11][CH:17]([C:16]([O:15][CH3:14])=[O:24])[CH2:19][S:20][C:21](=[O:23])[CH3:22])=[O:13])=[CH:6][CH:5]=1)[CH3:1]

Komponenten

7

Edukt 4

HCID 7468p-AminoacetophenoneHCID 9005Trimethyl orthoformateHCID 443297Hydroxyamine hydrochlorideHCID 86741874HCID 86741874, Verbindung

Produkt 1

HCID 86741882HCID 86741882, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 2.7 g 4-aminoacetophenone in 40 mL THF is added dropwise to a solution of 0.02 mol of S-acetylcysteine methyl 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'-[1-methoxycarbonyl-2-(acetylthio)ethyl]urea, 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-a5828d53eeea46d7a180d36272f53566
Quelldatensatz
uspto-grants-1988_04
Patentnummer
US04740611

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