Nitric Acid → 3-(5-Methyl-1,3,4-thiadiazol-2-yl)-5-nitro-1,2-benzisothiazole

HRID 48988Notes

Reaction equation

HRID 48988 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[S:9][N:8]=2)=[N:4][N:3]=1.S(=O)(=O)(O)O.[N+:21]([O-])([OH:23])=[O:22]>C(Cl)Cl>[CH3:1][C:2]1[S:6][C:5]([C:7]2[C:11]3[CH:12]=[C:13]([N+:21]([O-:23])=[O:22])[CH:14]=[CH:15][C:10]=3[S:9][N:8]=2)=[N:4][N:3]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 103991023-(5-Methyl-1,3,4-thiadiazol-2-yl)-1,2-benzisothiazole

Product 1

HCID 206342703-(5-Methyl-1,3,4-thiadiazol-2-yl)-5-nitro-1,2-benzisothiazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3-(5-methyl-1,3,4-thiadiazol-2-yl)-1,2-benzisothiazole(6.8 g, 0.0291 mol) and conc. sulfuric acid at 10° C. is added 90% nitric acid (3.20 ml, 0.582 mol) dropwise. The resultant mixture is stirred 90 min at 0-10° C. and poured into ice water with stirring. Filtration affords a solid which is stirred in hot methylene chloride and filtered to afford the title compound as a tan solid (mp 239-240° C.) which is identified by NMR analysis.

Workup

  1. filtrationFiltration
  2. customaffords a solid which
  3. filtrationfiltered

Sources & evidence

ORD record
ord-eeb9a78fc2024dd0a9d38a1a327d9be4
Source dataset
uspto-grants-2004_03
Patent number
US06706663B2

Reaction notes

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