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

HRID 848930Notes

Reaction equation

HRID 848930 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)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

First, a mixture containing 6.4 g of 2-(4-trifluoromethoxyphenyl)-4-iso-thiazolin-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 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 a 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-e2322da0f16a4d159fbe72f2fc4d564d
Source dataset
uspto-grants-2000_01
Patent number
US06010693

Reaction notes

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