Methyl iodide → 4-(2-Methyl-2H-tetrazol-5-yl)-benzaldehyde

HRID 380216Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 380216
[NH:1]1[C:5]([C:6]2[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][CH:7]=2)=[N:4][N:3]=[N:2]1.[C:14]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C.O1CCOCC1>[CH3:14][N:3]1[N:2]=[N:1][C:5]([C:6]2[CH:7]=[CH:8][C:9]([CH:10]=[O:11])=[CH:12][CH:13]=2)=[N:4]1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27606064-(1H-1,2,3,4-tetrazol-5-yl)benzaldehyde

Produkt 1

HCID 104878484-(2-Methyl-2H-tetrazol-5-yl)-benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 217120691,4-dioxane N,N-dimethylformamideLösungsmittel2×

Versuchsvorschrift

With ice-cooling, a solution of 75.5 g (0.434 mol) of 4-(tetrazol-5-yl)-benzaldehyde (Example 25a) in 550 ml of DMF/dioxane 1:1 is added dropwise to 179.7 g (1.30 mol) of K2CO3 in 200 ml of DMF/dioxane 1:1; the mixture is stirred for 30 min and then 40 ml (0.64 mol) of methyl iodide are added. The mixture is stirred in an ice bath for 3 hours and, finally, at room temperature for 15 hours; the reaction mixture is poured into 2.8 liters of ice-water and stirred for 10 min; the title compound is filtered off and washed with water: m.p.: 137-139° C.; 1H-NMR (CD3OD/CDCl3) d 10.05 (s, HCO), 8.29 and 8.03 (2d, J=8, each 2H), 4.43 (s, 3H).

Aufarbeitung

  1. temperatureWith ice-cooling
  2. stirringThe mixture is stirred in an ice bath for 3 hours
  3. waitfinally, at room temperature for 15 hours
  4. stirringstirred for 10 min
  5. filtrationthe title compound is filtered off
  6. washwashed with water

Quellen und Nachweise

ORD-Eintrag
ord-82c6b92e009e40369e68e7bed23cbd41
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06300519B1

Notizen zur Reaktion

Wird geladen…