Nitric Acid → 2(3H)-Benzothiazolone, 6-nitro-

Reaction equation

[S:1]1(=O)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[N+:11]([O-])([OH:13])=[O:12].C(OC(=O)C)(=[O:17])C>>[N+:11]([C:7]1[CH:8]=[CH:9][C:4]2[NH:3][C:2](=[O:17])[S:1][C:5]=2[CH:6]=1)([O-:13])=[O:12]

Participants

Reactant 3

HCID 944Nitric Acid

HCID 7918Acetic Anhydride

HCID 53400715Benzothiazolinone

Product 1

HCID 6415712(3H)-Benzothiazolone, 6-nitro-

Conditions

Temperature: -10 °C

Procedure

0.1 mol of benzothiazolinone is dissolved in 100 ml of acetic anhydride and the solution is cooled to −10° C. 10 ml of nitric acid are then added dropwise, and the reaction is stirred for 2 hours. The resulting precipitate is filtered off and washed with water, and then purified by chromatography (eluant CH2Cl2 then AcOEt) to yield the title product, which is recrystallised from ethanol.