2-Mercaptoethanol → 6,7-Dimethoxy-4-(3,4-dimethoxyphenyl)-2-(2-hydroxyethylthiomethyl)quinazoline

HRID 1458911Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1458911
Cl[CH2:2][C:3]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=2)[C:10]2[C:5](=[CH:6][C:7]([O:25][CH3:26])=[C:8]([O:23][CH3:24])[CH:9]=2)[N:4]=1.[SH:27][CH2:28][CH2:29][OH:30].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:24][O:23][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][C:7]=1[O:25][CH3:26])[N:4]=[C:3]([CH2:2][S:27][CH2:28][CH2:29][OH:30])[N:12]=[C:11]2[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=1

Komponenten

6

Edukt 4

HCID 15672-MercaptoethanolHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 107856562-Chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinazoline

Produkt 1

HCID 218511326,7-Dimethoxy-4-(3,4-dimethoxyphenyl)-2-(2-hydroxyethylthiomethyl)quinazolineAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 2-chloromethyl-6,7-dimethoxy-4-(3,4-dimethoxyphenyl)quinazoline (4.5 g), 2-mercaptoethanol (1.13 g), potassium carbonate (2.8 g) and N,N-dimethylformamide (50 ml) was stirred at room temperature for 2 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried over magnesium sulfate. Evaporation of the solvent gave 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2-(2-hydroxyethyl-thiomethyl)quinazoline (4.1 g, 82%) which was then recrystallized from ethanol. Colorless prisms. mp. 154°-155° C.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customEvaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-c9c41f586fa44601b396a9575f946c7c
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05852039

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