Trifluoroacetic anhydride → HCID 21697694, compound

HRID 378985Notes

Reaction equation

HRID 378985 reaction equation
[O:1]=[S:2]1(=[O:15])[CH:6]([CH2:7][CH2:8][CH3:9])[C:5]2[C:10]([Cl:14])=[CH:11][CH:12]=[CH:13][C:4]=2[NH:3]1.[N+:16]([O-])([O-:18])=[O:17].[NH4+].FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)(Cl)Cl>[O:15]=[S:2]1(=[O:1])[CH:6]([CH2:7][CH2:8][CH3:9])[C:5]2[C:10]([Cl:14])=[CH:11][CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[C:4]=2[NH:3]1

Participants

5

Reactant 3

HCID 9845Trifluoroacetic anhydrideHCID 22985Ammonium nitrateHCID 21697687HCID 21697687, compound

Product 1

HCID 21697694HCID 21697694, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

1,3-dihydro-2,2-dioxo-4-chloro-3-propyl-2,1 -benzisothiazole (131 mg, 0.54 mmol) was dissolved in chloroform (30 ml) followed by the addition of ammonium nitrate (44 mg, 0.54 mmol) and trifluoroacetic anhydride (397 mg, 214.4 mmol). The mixture is allowed to stir. After 24 hours, the reaction mixture is diluted with chloroform 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 (28 mg, 20%). EI-MS m/z 289.1 (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-8ede7c19c2f247f6bab83de31066875b
Source dataset
uspto-grants-2001_10
Patent number
US06297265B2

Reaction notes

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