Nitric Acid → 2-(Methoxymethyl)-6-nitro-1,3-benzothiazole
Reaktionsgleichung
[CH3:1][O:2][CH2:3][C:4]1[S:5][C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[N:8]=1.[N+:13]([O-])([OH:15])=[O:14]>S(=O)(=O)(O)O>[CH3:1][O:2][CH2:3][C:4]1[S:5][C:6]2[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:7]=2[N:8]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a cooled (0° C.) solution of 2-methoxymethyl-benzothiazole (2.4 g, 13.4 mmol) in concentrated sulfuric acid (8 mL) was added a mixture of 90% fuming nitric acid (2 mL) and concentrated sulfuric acid (1.3 mL) at a rate to keep the internal temperature below 5° C. After the addition was completed, the reaction mixture was stirred for 15 min at 0° C. and then at RT for 2 h. The mixture was poured into ice cold water. Collection of the precipitated solid by filtration, washing with cold water until the pH of the eluent was neutral, afforded 2.6 g (79%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 8.8 (d, J=2.1 Hz, 1H), 8.36 (dd, J=9, 2.1 Hz, 1H), 8.08 (d, J=9 Hz, 1H), 4.90 (s, 2H), 3.59 (s, 3H).