Pyridine → 3-(3,5-Dimethylpyrazol-1-yl)-5-nitro-1,2-benzisothiazole

HRID 48978

Reaction equation

HRID 48978 reaction equation
Cl[C:2]1[C:6]2[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=[CH:10][C:5]=2[S:4][N:3]=1.[CH3:14][C:15]1[CH:19]=[C:18]([CH3:20])[NH:17][N:16]=1.N1C=CC=CC=1>C(OCC)(=O)C>[CH3:14][C:15]1[CH:19]=[C:18]([CH3:20])[N:17]([C:2]2[C:6]3[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=[CH:10][C:5]=3[S:4][N:3]=2)[N:16]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 62103,5-DimethylpyrazoleHCID 1980981,2-Benzisothiazole, 3-chloro-5-nitro-

Product 1

HCID 206342663-(3,5-Dimethylpyrazol-1-yl)-5-nitro-1,2-benzisothiazoleYield 43.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-chloro-5-nitrobenzisothiazole (5.3 g, mmol), 3,5-dimethylpyrazole (2.40 g, 25.0 mmol) and pyridine is stirred overnight at reflux, cooled to room temperature and diluted with ethyl acetate. The resultant mixture is filtered and the filtrate is washed with three portions of 10% hydrochloric acid and one portion of water. The organic layer is dried over anhydrous magnesium sulfate and concentrated in vacuo to afford the title compound (2.85 g, 43.8%) which is identified by NMR spectral analysis.

Workup

  1. temperatureat reflux
  2. filtrationThe resultant mixture is filtered
  3. washthe filtrate is washed with three portions of 10% hydrochloric acid and one portion of water
  4. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2faec26a94d54e92a133e6d5e439322b
Source dataset
uspto-grants-2004_03
Patent number
US06706663B2

Linked notes

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