Sulfuric Acid → 1,3-Dihydro-2,2-dioxo-4-chloro-7-nitro-2,1-benzisothiazole

HRID 378986Notes

Reaction equation

HRID 378986 reaction equation
[O:1]=[S:2]1(=[O:12])[CH2:6][C:5]2[C:7]([Cl:11])=[CH:8][CH:9]=[CH:10][C:4]=2[NH:3]1.[N+:13]([O-])([O-:15])=[O:14].[Na+].S(=O)(=O)(O)O.N([O-])=O.[Na+]>C(Cl)Cl>[O:12]=[S:2]1(=[O:1])[CH2:6][C:5]2[C:7]([Cl:11])=[CH:8][CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[C:4]=2[NH:3]1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 24268Sodium NitrateHCID 217951722,1-Benzisothiazole, 4-chloro-1,3-dihydro-, 2,2-dioxideHCID 23668193Sodium Nitrite

Product 1

HCID 98163551,3-Dihydro-2,2-dioxo-4-chloro-7-nitro-2,1-benzisothiazoleYield 21.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1 ,3-dihydro-2,2-dioxo-4-chloro-2,1-benzisothiazole (1.5 mg, 0.92 mmol) was dissolved in methylene chloride (30 ml) followed by the addition of sodium nitrate (86 mg, 1.01 mmol). The addition of sulfuric acid (0.18 ml/3M) is then made, followed by addition of a catalytic amount of sodium nitrite. The mixture is allowed to stir. After about 24 hours, the reaction mixture is diluted with methylene chloride and extracted with water. The organic layer is dried over MgSO4 and filtered. The solvent was evaporated and chromatography of the resulting solid on silica gel (50% Ethyl acetate/Hexane) gave the desired product(50 mg, 21%). EI-MS m/z 263.5 (M+).

Workup

  1. extractionextracted with water
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-35eb12a25dff4b168e43cd5d672b3864
Source dataset
uspto-grants-2001_10
Patent number
US06297265B2

Reaction notes

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