4-Cyanobenzaldehyde → HCID 137167455, Verbindung

HRID 59049

Reaktionsgleichung

Reaktionsgleichung von HRID 59049
[CH3:1][C:2]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N:18]3[C:22](=[O:23])[NH:21][N:20]=[N:19]3)[CH:13]=2)[C:10](=[O:24])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[C:25]([C:27]1[CH:34]=[CH:33][C:30]([CH:31]=O)=[CH:29][CH:28]=1)#[N:26]>CC(O)=O>[O:24]=[C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2](/[CH:1]=[CH:31]/[C:30]2[CH:33]=[CH:34][C:27]([C:25]#[N:26])=[CH:28][CH:29]=2)[N:11]1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N:18]2[C:22](=[O:23])[NH:21][N:20]=[N:19]2)[CH:13]=1

Komponenten

4

Edukt 2

HCID 660424-CyanobenzaldehydeHCID 1371674492-methyl-3-(3-(5-oxo-4,5-dihydro-1H-tetrazol-yl)phenyl)quinazolin-4(3H)-one

Produkt 1

HCID 137167455HCID 137167455, VerbindungAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux
  3. customafter 3 hr
  4. temperatureAfter cooling
  5. custompurified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-c62a9dd335814ee6973cba7297d17721
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09439888B2

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