Water → HCID 18314471, compound

HRID 277381Notes

Reaction equation

HRID 277381 reaction equation
[CH3:1][C:2]([CH3:17])([C:5]1[C:9]2[CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=[CH:13][C:8]=2[S:7][N:6]=1)[C:3]#N.[OH2:18].S(=O)(=O)(O)O.[C:24](=[O:27])(O)[O-].[Na+].[CH2:29](Cl)Cl>C(O)C>[CH3:1][C:2]([CH3:17])([C:5]1[C:9]2[CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=[CH:13][C:8]=2[S:7][N:6]=1)[C:3]([O:27][CH2:24][CH3:29])=[O:18]

Participants

7

Reactant 5

HCID 962WaterHCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 18314504HCID 18314504, compound

Product 1

HCID 18314471HCID 18314471, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of α,α-dimethyl-5-nitro-1,2-benzisothiazole-3-acetonitrile (0.913 g, 3.69 mmol), water (0.450 mL), concentrated sulfuric acid (4.55 mL) and ethanol (9.10 mL) is refluxed for one hour, cooled, and poured onto ice. The resultant aqueous mixture is neutralized with saturated sodium bicarbonate solution and extracted with methylene chloride. The organic extract is washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo to obtain a solid. Column chromatography of the solid using silica gel and methylene chloride gives the title product as pale yellow crystals.

Workup

  1. temperatureis refluxed for one hour
  2. temperaturecooled
  3. additionpoured onto ice
  4. extractionextracted with methylene chloride
  5. extractionThe organic extract
  6. washis washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customto obtain a solid

Sources & evidence

ORD record
ord-1ee09b1d9002456f873037ace099849f
Source dataset
uspto-grants-2002_03
Patent number
US06355796B1

Reaction notes

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