Dimethylformamide → 2-[3-(4-Chlorobenzoyl)benzyl]thio-3-methyl-4(3H)-quinazolinone

HRID 1291243Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1291243
[SH:1][C:2]1[N:11]([CH3:12])[C:10](=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[OH-].[Na+].CN(C=O)C.[Cl:21][C:22]1[CH:37]=[CH:36][C:25]([C:26]([C:28]2[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=2)[CH2:31]Br)=[O:27])=[CH:24][CH:23]=1>C(O)C.O>[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([C:26]([C:28]2[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=2)[CH2:31][S:1][C:2]2[N:11]([CH3:12])[C:10](=[O:13])[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)=[O:27])=[CH:36][CH:37]=1

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 136496533-(4-Chlorobenzoyl)benzyl bromideHCID 178481666HCID 178481666, Verbindung

Produkt 1

HCID 189190432-[3-(4-Chlorobenzoyl)benzyl]thio-3-methyl-4(3H)-quinazolinoneAusbeute 101,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 2-mercapto-3-methyl-4(3H)-quinazolinone (1.0 g) and sodium hydroxide (250 mg) in 50% ethanol (15 ml)-DMF (15 ml) was added 3-(4-chloro-benzoyl)benzyl bromide (1.88 g) and the mixture was stirred at room temperature for 1 hour. This reaction mixtrue was poured in water and the resulting crystals were collected by filtration, rinsed with water and methanol, and recrystallized from methanol to provide the title compound as colorless solid (2.22 g). 1H-NMR (CDCl3) 8: 3.59(3H,s), 4.59(2H,s), 7.34-7.52(5H,m), 7.61-7.80(5H,m), 7.96(1H,d,J=2.0Hz), 8.22(1H,dd,J=8.0,1.4Hz).

Aufarbeitung

  1. filtrationthe resulting crystals were collected by filtration
  2. washrinsed with water and methanol
  3. customrecrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-30e89e1420e14406861d683c91356859
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05753664

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