반응 #87327

반응 방정식

2-methyl-3-(3-(5-oxo-4,5-dihydro-1H-tetrazol-1-yl)phenyl)quinazolin-4(3H)-one

4-cyanobenzaldehyde

→

desired product

수율 70.0%

(E)-4-(2-(4-oxo-3-(3-(5-oxo-4,5-dihydro-1H-tetrazol-1-yl)phenyl)-3,4-dihydroquinazolin-2-yl)vinyl)benzonitrile

수율 70.0%

용매

AcOH

반응 조건

후처리

1. 1
   온도was heated
2. 2
   온도to reflux
3. 3
   기타after 3 hr
4. 4
   온도After cooling
5. 5
   기타purified by column chromatography on silica gel

실험 절차

A mixture of 2-methyl-3-(3-(5-oxo-4,5-dihydro-1H-tetrazol-1-yl)phenyl)quinazolin-4(3H)-one (32 mg, 0.1 mmol) and 4-cyanobenzaldehyde (16 mg, 0.12 mmol) in AcOH (5 mL) was heated to reflux and stirred for 3 days (continuously monitored by LC/MS, which indicated product formation after 3 hr). After cooling, the mixture was dry-loaded onto silica gel and purified by column chromatography on silica gel using CH2Cl2/MeOH (1:0 to 95:5) as eluent to give a solid (11 mg; desired product ca. 70% purity). The solid was re-purified by preparative thin-layer chromatography using CH2Cl2/MeOH (9:1) as eluent to give the product (6 mg, 14%) as a solid.

출처