Sulfuric Acid → HCID 11118891, compound

HRID 378983Notes

Reaction equation

HRID 378983 reaction equation
[O:1]=[S:2]1(=[O:13])[CH:6]([CH3:7])[C:5]2[C:8]([Cl:12])=[CH:9][CH:10]=[CH:11][C:4]=2[NH:3]1.[N+:14]([O-])([O-:16])=[O:15].[Na+].S(=O)(=O)(O)O.N([O-])=O.[Na+]>C(Cl)Cl>[O:13]=[S:2]1(=[O:1])[CH:6]([CH3:7])[C:5]2[C:8]([Cl:12])=[CH:9][CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[C:4]=2[NH:3]1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 24268Sodium NitrateHCID 21697691HCID 21697691, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 11118891HCID 11118891, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1,3-dihydro-2,2-dioxo-4-chloro-3-methyl-2,1-benzisothiazole (200 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-333c7cff5df5460ba847dd5d7776d17c
Source dataset
uspto-grants-2001_10
Patent number
US06297265B2

Reaction notes

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