Dimethyl Sulfide → 6-nitro-3,4-dihydro-2H-1,4-benzoxazine
Reaktionsgleichung
S(C)C.[N+:4]([C:7]1[CH:8]=[CH:9][C:10]2[O:15][CH2:14][C:13](=O)[NH:12][C:11]=2[CH:17]=1)([O-:6])=[O:5]>C1COCC1>[N+:4]([C:7]1[CH:8]=[CH:9][C:10]2[O:15][CH2:14][CH2:13][NH:12][C:11]=2[CH:17]=1)([O-:6])=[O:5]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of BH3.Me2S in THF (2 M, 7.75 mL, 15.5 mmol) was added dropwise to a suspension of 6-nitro-4H-benzo[1,4]oxazin-3-one (0.6 g, 3.1 mmol) in THF (10 mL). The mixture was stirred at room temperature overnight. The reaction was quenched with MeOH (5 mL) at 0° C. and then water (20 mL) was added. The mixture was extracted with Et2O and the combined organic layers were washed with brine, dried over Na2SO4 and concentrated to give 6-nitro-3,4-dihydro-2H-benzo[1,4]oxazine as a red solid (0.5 g, 89%), which was used without further purification.