Acetonitrile → HCID 20634277, compound

HRID 48979Notes

Reaction equation

HRID 48979 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:11][N:10]=[C:9]([N:12]3[CH:16]=[CH:15][C:14]([CH3:17])=[N:13]3)[C:8]=2[CH:18]=1)([O-])=O.C(=O)(O)[O-].[Na+].C(#N)C.S(S([O-])=O)([O-])=O.[Na+].[Na+]>C(OCC)(=O)C.O>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[S:11][N:10]=[C:9]([N:12]3[CH:16]=[CH:15][C:14]([CH3:17])=[N:13]3)[C:8]=2[CH:18]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 206342785-Nitro-3-(3-methylpyrazol-1-yl)-1,2-benzisothiazole

Product 1

HCID 20634277HCID 20634277, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 5-nitro-3-(3-methylpyrazol-1-yl)-1,2-benzisothiazole (3.12 g, 12.0 mmol), sodium bicarbonate (2.00 g, 23.8 mmol), acetonitrile and water is stirred one hour at 70° C. and treated with sodium hydrosulfite (8.70 g, 50.0 mmol) in portions. The resultant mixture is stirred overnight at reflux, cooled to room temperature and diluted with ethyl acetate. The organic layer is dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue is washed with a mixture of methylene chloride and ethyl acetate. The organic layer is decanted to afford the title compound as a viscous brown oil which is identified by NMR spectral analysis.

Workup

  1. temperatureat reflux
  2. temperaturecooled to room temperature
  3. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. washThe residue is washed with a mixture of methylene chloride and ethyl acetate
  6. customThe organic layer is decanted

Sources & evidence

ORD record
ord-4820fec84905457887f6c476a3246362
Source dataset
uspto-grants-2004_03
Patent number
US06706663B2

Reaction notes

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