Triethyloxonium tetrafluoroborate → 5,6-Dimethoxy-3-ethoxy-benzoisothiazole-1,1-dioxide

HRID 280556Notes

Reaction equation

HRID 280556 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[S:8](=[O:10])(=[O:9])[NH:7][C:6]2=[O:16].F[B-](F)(F)F.[CH2:22]([O+](CC)CC)[CH3:23]>ClCCl>[CH3:1][O:2][C:3]1[C:13]([O:14][CH3:15])=[CH:12][C:11]2[S:8](=[O:9])(=[O:10])[N:7]=[C:6]([O:16][CH2:22][CH3:23])[C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 2723982Triethyloxonium tetrafluoroborateHCID 470031361,2-Benzisothiazol-3(2H)-one, 5,6-dimethoxy-, 1,1-dioxide

Product 1

HCID 233207605,6-Dimethoxy-3-ethoxy-benzoisothiazole-1,1-dioxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5,6-dimethoxysaccharin (0.8 g) in dichloromethane (100 ml) was added triethyloxonium tetrafluoroborate (3.5 ml, 1M soln in CH2Cl2) and the solution stirred at room temperature for 3 hrs. After extraction with aqueous sodium bicarbonate, the organic phase was dried and concentrated. Purification by column chromatography (silica, chloroform) gave the title compound (0.2 g).

Workup

  1. extractionAfter extraction with aqueous sodium bicarbonate
  2. customthe organic phase was dried
  3. concentrationconcentrated
  4. customPurification by column chromatography (silica, chloroform)

Sources & evidence

ORD record
ord-0f970589eafc4013b0fddabf1e25ff9d
Source dataset
uspto-grants-1986_05
Patent number
US04590192

Reaction notes

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