Dimethylformamide → HCID 19806696, compound

HRID 1681466Notes

Reaction equation

HRID 1681466 reaction equation
[CH2:1]([O:3][C:4]1[C:8]([Cl:9])=[C:7](Cl)[S:6][N:5]=1)[CH3:2].[CH3:11][S:12][O-:13].[Na+].CN(C=[O:19])C>C(OCC)C>[CH2:1]([O:3][C:4]1[C:8]([Cl:9])=[C:7]([S:12]([CH3:11])(=[O:19])=[O:13])[S:6][N:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 19806678HCID 19806678, compoundHCID 23717576HCID 23717576, compound

Product 1

HCID 19806696HCID 19806696, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-ethoxy-4,5-dichloroisothiazole (19.8 g, 0.10 mol) in DMF (50 ml) under a nitrogen atmosphere was added sodium methanesulfenate (20.4 g, 0.20 mol). The mixture was warmed to 100° C. and stirred for two days. The reaction mixture was then cooled, diluted with diethyl ether, washed with water, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed on a silica gel column, eluting with chloroform, to give 7.1 g of the title compound, mp 85°-87° , crystallized from cyclohexane. A by-product, 3-ethoxy-4,5-bis(methylsulfonyl)isothiazole (3.9 g) was also obtained, mp 158°-160° (crystallized from cyclohexane).

Workup

  1. temperatureThe reaction mixture was then cooled
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on a silica gel column
  7. washeluting with chloroform

Sources & evidence

ORD record
ord-26c8de8e610746339adcc9475d618aed
Source dataset
uspto-grants-1992_12
Patent number
US05171860

Reaction notes

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