Sulfuryl chloride → 4,5-Dichloro-2-[4-(trifluoromethoxy)phenyl]-1,2-thiazol-3(2H)-one

HRID 741646Notes

Reaction equation

HRID 741646 reaction equation
FC(F)(F)OC1C=CC(N2C(=O)C=CS2)=CC=1.[F:18][C:19]([F:35])([F:34])[O:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]2[C:31](=[O:32])[CH:30]=[C:29]([Cl:33])[S:28]2)=[CH:23][CH:22]=1.S(Cl)([Cl:39])(=O)=O.C(=O)([O-])O.[Na+]>ClCCl>[F:35][C:19]([F:18])([F:34])[O:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]2[C:31](=[O:32])[C:30]([Cl:39])=[C:29]([Cl:33])[S:28]2)=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 24648Sulfuryl chlorideHCID 516892Sodium BicarbonateHCID 98816503(2H)-Isothiazolone, 2-[4-(trifluoromethoxy)phenyl]-HCID 15390069HCID 15390069, compound

Product 1

HCID 153900704,5-Dichloro-2-[4-(trifluoromethoxy)phenyl]-1,2-thiazol-3(2H)-oneYield 70.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

First, a mixture containing 6.4 g of 2-(4-trifluorornethoxyphenyl)-4-isothiazolin-3-on and 5.1 g of 2-(4-trifluoromethoxyphenyl)-5-chloro-4-isothiazolin-3-on was suspended in 100 ml of dichloromethane, after which 19 g of sulfuryl chloride was then added dropwise to the suspension dropwise at room temperature, and the resultant mixture was stirred for 12 hours. After completion of the reaction, 200 ml of a saturated aqueous solution of sodium hydrogencarbonate was added to the reaction mixture, and the dichloromethane layer was separated. The aqueous layer was extracted with 150 ml of dichloromethane. The combined dichloromethane layer was washed with water, dried with magnesium sulfate, and concentrated. The concentrate was purified by column chromatography (hexane: ethyl acetate=6:1) to give 4 g of 2-(4-trifluoromethoxyphenyl)-4,5-dichloro-4-isothiazolin-3-on (compound (13); m.p., 129°-130° C.).

Workup

  1. additionwas added to the reaction mixture
  2. customthe dichloromethane layer was separated
  3. extractionThe aqueous layer was extracted with 150 ml of dichloromethane
  4. washThe combined dichloromethane layer was washed with water
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated
  7. customThe concentrate was purified by column chromatography (hexane: ethyl acetate=6:1)

Sources & evidence

ORD record
ord-ca520151006e442bb3181e28c04c38b5
Source dataset
uspto-grants-1996_09
Patent number
US05552423

Reaction notes

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