Nitric Acid → 2-Chloro-6-nitrobenzothiazole

HRID 1791939Notes

Reaction equation

HRID 1791939 reaction equation
S(=O)(=O)(O)O.[Cl:6][C:7]1[S:8][C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[N:11]=1.[N+:16]([O-])([OH:18])=[O:17]>O>[Cl:6][C:7]1[S:8][C:9]2[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:10]=2[N:11]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 119872-Chlorobenzothiazole

Product 1

HCID 754762-Chloro-6-nitrobenzothiazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Conc. sulfuric acid (50 mL) was added to 2-chlorobenzothiazole (10 g) under ice-cooling, and conc. nitric acid (5 mL) was added dropwise under ice-cooling. The mixture was stirred under ice-cooling for 1 hr, and iced water (600 mL) was added to the reaction mixture. The precipitated solid was collected by filtration, which was then recrystallized from acetone to give 2-chloro-6-nitrobenzothiazole (6.36 g) as a pale-yellow powder.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. temperaturecooling for 1 hr
  4. filtrationThe precipitated solid was collected by filtration, which
  5. customwas then recrystallized from acetone

Sources & evidence

ORD record
ord-219e30c1dca24637845e5b3d4c9459db
Source dataset
uspto-grants-2006_07
Patent number
US07074794B2

Reaction notes

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