Nitric Acid → 6-Nitrobenzothiazole

HRID 353018

Reaction equation

HRID 353018 reaction equation
C[C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[N+:11]([O-])([OH:13])=[O:12]>S(=O)(=O)(O)O>[N+:11]([C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[CH:2][S:3][C:4]=2[CH:10]=1)([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 84462-Methylbenzothiazole2×

Product 1

HCID 762566-Nitrobenzothiazole

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

See FIG. 3A. Nitration of 2-methylbenzothiazole was performed following the method of Mizuno, J. Pharm. Soc. Japan, 72, 745 (1952). A mixture of fuming nitric acid (1.6 mL) and concentrated sulfuric acid (1.2 mL) was added to an ice-cooled solution of 2-methylbenzothiazole (2 g) in sulfuric acid (8 mL). The solution was allowed to warm to room temperature for one hour, then poured onto 100 mL of ice. The solid was filtered, washed with water, and recrystallized from ethanol (80 mL) to provide 2.5 g of yellowish needles.

Workup

  1. filtrationThe solid was filtered
  2. washwashed with water
  3. customrecrystallized from ethanol (80 mL)

Sources & evidence

ORD record
ord-2ed0bbd2a51e40069fca902b09766555
Source dataset
uspto-grants-2004_06
Patent number
US06750024B2

Linked notes

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