Nitric Acid → HCID 22402903, compound

HRID 375079Notes

Reaction equation

HRID 375079 reaction equation
[CH3:1][CH:2]([C:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[S:9][N:8]=1)[C:3]([O:5][CH3:6])=[O:4].[N+:16]([O-])([OH:18])=[O:17]>>[CH3:1][CH:2]([C:7]1[C:11]2[CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=[CH:15][C:10]=2[S:9][N:8]=1)[C:3]([O:5][CH3:6])=[O:4]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 22402908HCID 22402908, compound

Product 1

HCID 22402903HCID 22402903, compound

Procedure

Methyl α-methyl-1,2-benzisothiazole-3-acetate (15.96 g, 72.13 mmol) is added dropwise to nitric acid (90%, 100 mL) while maintaining the reaction mixture temperature below 5° C. The reaction mixture is stirred overnight, poured onto ice and extracted with methylene chloride. The organic extracts are combined, washed sequentially with water, saturated sodium hydrogen carbonate solution and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain an orange oil. Column chromatography of the oil using silica gel and ether/hexanes solutions gives the title product as an orange solid, mp 88°-90° C.

Workup

  1. temperaturewhile maintaining the reaction mixture temperature below 5° C
  2. additionpoured onto ice
  3. extractionextracted with methylene chloride
  4. washwashed sequentially with water, saturated sodium hydrogen carbonate solution and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto obtain an orange oil

Sources & evidence

ORD record
ord-7714b6a2fd0d4f91ab8f646cc0f30e42
Source dataset
uspto-grants-1996_01
Patent number
US05484763

Reaction notes

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