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

HRID 477600

Reaction equation

HRID 477600 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

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

Workup

  1. customat a temperature of 0° to 5° C.
  2. filtrationThe precipitated crystals were collected by filtration
  3. washwashed with water
  4. customair-dried

Sources & evidence

ORD record
ord-4d7894b18cae4d32a9134e8990bf4b1d
Source dataset
uspto-grants-1989_12
Patent number
US04888428

Linked notes

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