3,4-Dichloro-2-methyl-5-ethoxycarbonylisothiazolium fluorosulfonate → 4-Chloro-5-ethoxycarbonyl-2-methyl-4-isothiazolin-3-one

HRID 1980367Notes

Reaction equation

HRID 1980367 reaction equation
FS([O-])(=O)=[O:3].Cl[C:7]1[C:11]([Cl:12])=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[S:9][N+:8]=1[CH3:18]>C([O-])([O-])=O.[K+].[K+]>[Cl:12][C:11]1[C:7](=[O:3])[N:8]([CH3:18])[S:9][C:10]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

3

Reactant 1

HCID 128890133,4-Dichloro-2-methyl-5-ethoxycarbonylisothiazolium fluorosulfonate

Product 1

HCID 128890594-Chloro-5-ethoxycarbonyl-2-methyl-4-isothiazolin-3-oneYield 37.6%

Reagents, catalysts & solvents 1

HCID 11430Potassium CarbonateSolvent

Procedure

3,4-Dichloro-5-ethoxycarbonyl-2-methylisothiazolium fluorosulfonate (4.2 g, 0.012 mol) was added to 50 ml of saturated K2CO3 solution. The aqueous phase was extracted wih 3×50 ml of CH2Cl2. The combined extracts were dried (MgSO4), filtered and conc. to yield a solid. Recrystallization from heptane yielded 1.0 g (35%) of 4-chloro-5-ethoxycarbonyl-2-methyl-4-isothiazolin-3-one, mp 142-147.

Workup

  1. extractionThe aqueous phase was extracted wih 3×50 ml of CH2Cl2
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. filtrationfiltered
  4. customconc. to yield a solid
  5. customRecrystallization from heptane

Sources & evidence

ORD record
ord-d11a09f8d43c4fe780a47874f998308f
Source dataset
uspto-grants-1985_04
Patent number
US04508908

Reaction notes

Loading…