Nitric Acid → 6-Nitrobenzothiazole

HRID 1422196Notes

Reaction equation

HRID 1422196 reaction equation
[N+:1]([O-:4])(O)=[O:2].C[C:6]1[S:7][C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[N:10]=1>S(=O)(=O)(O)O>[N+:1]([C:13]1[CH:12]=[CH:11][C:9]2[N:10]=[CH:6][S:7][C:8]=2[CH:14]=1)([O-:4])=[O:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 84462-Methylbenzothiazole

Product 1

HCID 762566-Nitrobenzothiazole

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

See FIG. 3A. Nitration of 2-methylbenzothizole 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-39f10004659d4300a60f8961e818926e
Source dataset
uspto-grants-2000_06
Patent number
US06080868

Reaction notes

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