Phosphorus oxychloride → 3-(5-Methyl-1,3,4-oxadiazol-2-yl)-5-nitro-1,2-benzisothiazole

HRID 48992Notes

Reaction equation

HRID 48992 reaction equation
[C:1]([NH:4][NH:5][C:6]([C:8]1[C:12]2[CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=[CH:16][C:11]=2[S:10][N:9]=1)=[O:7])(=O)[CH3:2].P(Cl)(Cl)(Cl)=O>C(#N)C>[CH3:2][C:1]1[O:7][C:6]([C:8]2[C:12]3[CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=[CH:16][C:11]=3[S:10][N:9]=2)=[N:5][N:4]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 206342531-Acetyl-2-[(5-nitro-1,2-benzisothiazol-3-yl)carbonyl]hydrazine

Product 1

HCID 206342693-(5-Methyl-1,3,4-oxadiazol-2-yl)-5-nitro-1,2-benzisothiazole

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 1-acetyl-2-[(5-nitro-1,2-benzisothiazol-3-yl)carbonyl]hydrazine(4.55 g, 0.0163 mol) and acetonitrile at room temperature is added phosphorous oxychloride (14.9 g, 0.0972 mol). The resultant mixture is heated to reflux, stirred two hours, cooled to room temperature and filtered to afford the title compound as an off-white solid (mp>250° C.) which is identified by NMR spectral analysis.

Workup

  1. temperatureto reflux
  2. filtrationfiltered

Sources & evidence

ORD record
ord-d8795f9d47814055bb529fdb58344c03
Source dataset
uspto-grants-2004_03
Patent number
US06706663B2

Reaction notes

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