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

HRID 896505

Reaction equation

HRID 896505 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

4

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 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.

Workup

  1. filtrationThe resulting precipitate is filtered off
  2. washwashed with water
  3. custompurified by chromatography (eluant CH2Cl2

Sources & evidence

ORD record
ord-1fbddb1298af4da6a2867526236a7614
Source dataset
uspto-grants-2005_07
Patent number
US06919362B2

Linked notes

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