Nitric Acid → Benzothiazole, 2-methyl-6-nitro-

HRID 2105097Notes

Reaction equation

HRID 2105097 reaction equation
[CH3:1][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>[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 84462-Methylbenzothiazole

Product 1

HCID 76250Benzothiazole, 2-methyl-6-nitro-

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

2-Methylbenzothiazole (22 g) in conc. sulfuric acid (80 ml) was cooled to −5° C. A mixture of conc. sulfuric acid (12 ml) in conc. nitric acid (20 ml) was added so as to maintain the temperature below 5° C. (ca. 1.5 hours). After this time the mixture was allowed to warm to room temperature and the solution poured onto ice to give a yellow precipitate. The solid was removed by filtration and recrystallised from ethanol. After filtration the solid was washed with ethanol and dried in a vacuum oven to give 18 g of the desired product.

Workup

  1. additionwas added so as
  2. temperatureto maintain the temperature below 5° C. (ca. 1.5 hours)
  3. additionthe solution poured onto ice
  4. customto give a yellow precipitate
  5. customThe solid was removed by filtration
  6. customrecrystallised from ethanol
  7. filtrationAfter filtration the solid
  8. washwas washed with ethanol
  9. customdried in a vacuum oven

Sources & evidence

ORD record
ord-87f7fa9d6aaf40ab95bf44e71d90cf1f
Source dataset
uspto-grants-2009_08
Patent number
US07579140B2

Reaction notes

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