Nitric Acid → 6-fluoro-5-nitro-2(3H)-benzothiazolone

HRID 1761812

Reaction equation

HRID 1761812 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]2[NH:6][C:7](=[O:9])[S:8][C:4]=2[CH:3]=1.[N+:12]([O-])([OH:14])=[O:13]>S(=O)(=O)(O)O>[F:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]2[NH:6][C:7](=[O:9])[S:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 446672-Benzothiazolinone, 6-fluoro-

Product 1

HCID 139579556-fluoro-5-nitro-2(3H)-benzothiazoloneYield 80.5%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 6-fluoro-2(3H)-benzothiazolone (47.58 g) in 100% sulfuric acid (760 ml) was cooled at 0° to 5° C., and 98% fuming nitric acid (d=1.52; 18.79 g) was dropwise added thereto, followed by stirring at the same temperatur for 60 minutes. The reaction mixture was poured into ice-water. The precipitated crystals were collected by filtration, washed with water and dried to give 6-fluoro-5-nitro-2(3H)-benzothiazolone (48.48 g) as pale brown crystals. m.p., 180°-182° C.

Workup

  1. filtrationThe precipitated crystals were collected by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-502f4cffdf864b9d845301fed04ec6f7
Source dataset
uspto-grants-1989_05
Patent number
US04828605

Linked notes

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