Reaktion #410535

Reaktionsgleichung

methyl 2-methoxy-5-aminobenzoate

sodium azide

triethyl orthoformate

→

methyl 2-methoxy-5-(1H-tetrazol-1-yl)benzoate

Lösungsmittel

water

acetic acid

acetic acid

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenconcentrate the reaction mixture in vacuo
2. 2
   Sonstigeto remove ethanol
3. 3
   workup.WAITAfter 1 hour
4. 4
   Temperaturto heat to 70° C
5. 5
   workup.WAITAfter an additional hour
6. 6
   Temperaturcool the reaction mixture to ambient temperature
7. 7
   SonstigeCollect the solid
8. 8
   Filtrationby filtration
9. 9
   Waschenrinse with water
10. 10
    Sonstigedry

Vorschrift

Combine methyl 2-methoxy-5-aminobenzoate (3.94 g, 21.7 mmol) and triethyl orthoformate (12.8 g, 86.7 mmol) in glacial acetic acid (20 mL). After 20 hours, concentrate the reaction mixture in vacuo to remove ethanol. Add glacial acetic acid (20 mL) and sodium azide (5.64 g, 86.7 mmol). Heat to 70° C. After 1 hour, add glacial acetic acid (10 mL) and continue to heat to 70° C. After an additional hour, cool the reaction mixture to ambient temperature, dilute with water (500 mL). Collect the solid by filtration, rinse with water, and dry to give methyl 2-methoxy-5-(1H-tetrazol-1-yl)benzoate.

Quelle