Nitric Acid → 6-fluoro-3-(5-methyl-1,2,4-oxadiazol-3-ylmethyl)-5-nitro-2(3H)-benzothiazolone

HRID 1199618

Reaction equation

HRID 1199618 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:5]2[N:6]([CH2:10][C:11]3[N:15]=[C:14]([CH3:16])[O:13][N:12]=3)[C:7](=[O:9])[S:8][C:4]=2[CH:3]=1.S(=O)(=O)(O)O.[N+:24]([O-])([OH:26])=[O:25]>C(OCC)(=O)C>[F:1][C:2]1[C:18]([N+:24]([O-:26])=[O:25])=[CH:17][C:5]2[N:6]([CH2:10][C:11]3[N:15]=[C:14]([CH3:16])[O:13][N:12]=3)[C:7](=[O:9])[S:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 199794996-fluoro-3-(5-methyl-1,2,4-oxadiazol-3-ylmethyl)-2(3H)-benzothiazolone

Product 1

HCID 199794886-fluoro-3-(5-methyl-1,2,4-oxadiazol-3-ylmethyl)-5-nitro-2(3H)-benzothiazoloneYield 96.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A compound of 6-fluoro-3-(5-methyl-1,2,4-oxadiazol-3-ylmethyl)-2(3H)-benzothiazolone (11.5 g) was added portionwise to concentrated sulfuric acid (200 g) which had been cooled to a temperature of 5° to 10° C. The reaction mixture was stirred at a temperature of 0° to 5° C. for 10 minutes. To the reaction mixture was dropwise added a 98% nitric acid (3 g). The reaction mixture was stirred at a temperature of 0° to 5° C. for 2 hours, and then poured onto ice. Ethyl acetate (1 liter) was added to the mixture, and the whole was stirred. The ethyl acetate layer was separated, washed with water, with a saturated aqueous sodium bicarbonate solution, and then with a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was recrystallized from ethanol, so that the aimed product, i.e. 6-fluoro-3-(5-methyl-1,2,4-oxadiazol-3-ylmethyl)-5 -nitro-2(3H)-benzothiazolone (13.0 g) was obtained. m.p. 192°-193° C.

Workup

  1. temperaturehad been cooled to a temperature of 5° to 10° C
  2. stirringThe reaction mixture was stirred at a temperature of 0° to 5° C. for 2 hours
  3. additionpoured onto ice
  4. stirringthe whole was stirred
  5. customThe ethyl acetate layer was separated
  6. washwashed with water, with a saturated aqueous sodium bicarbonate solution
  7. dry with materialwith a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off
  9. customthe residue was recrystallized from ethanol, so that the aimed product

Sources & evidence

ORD record
ord-3e957c0a09264b06bae7c37b88a4590e
Source dataset
uspto-grants-1990_02
Patent number
US04902335

Linked notes

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