3,5-Dinitroperbenzoic acid → 3-Methoxy-4-bromoisothiazole-1-oxide

HRID 1681474Notes

Reaction equation

HRID 1681474 reaction equation
[CH3:1][O:2][C:3]1[C:7]([Br:8])=[CH:6][S:5][N:4]=1.[N+](C1C=C([N+]([O-])=O)C=C(C(OO)=O)C=1)([O-])=[O:10]>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:7]([Br:8])=[CH:6][S:5](=[O:10])[N:4]=1

Participants

4

Reactant 2

HCID 101769383,5-Dinitroperbenzoic acidHCID 123939314-Bromo-3-methoxy-1,2-thiazole

Product 1

HCID 198066893-Methoxy-4-bromoisothiazole-1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-methoxy-4-bromoisothiazole (2.9 g, 15 mmol) in methylene chloride (15 ml) there can be was added, in portions, 3,5-dinitroperbenzoic acid (3.4 g, 15 mmol) with ice bath cooling. After about one hour, the precipitated 3,5-dinitrobenzoic acid can be filtered off and the solvent evaporated in vacuo. By triturating the residue with diethyl ether, a crystalline product, 3-methoxy-4-bromoisothiazole-1-oxide, can be obtained. Additional material can be obtained by chromatographing the mother liquors on silica gel, eluting with chloroform.

Workup

  1. temperaturecooling
  2. filtrationthe precipitated 3,5-dinitrobenzoic acid can be filtered off
  3. customthe solvent evaporated in vacuo
  4. customBy triturating the residue with diethyl ether

Sources & evidence

ORD record
ord-8193099e661c4196a7bab6f9bfbe0c85
Source dataset
uspto-grants-1992_12
Patent number
US05171860

Reaction notes

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