1,2-Dichloroethane → 4,5-Dichloro-2-octyl-1lambda~4~,2-thiazolidine-1,3-dione

HRID 461364Notes

Reaction equation

HRID 461364 reaction equation
[CH2:1]([N:9]1[C:13](=[O:14])C=C[S:10]1=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].S(Cl)(Cl)(=O)=O.[CH2:21]([Cl:24])[CH2:22][Cl:23]>>[Cl:23][CH:22]1[CH:21]([Cl:24])[S:10](=[O:15])[N:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[C:13]1=[O:14]

Participants

4

Reactant 3

HCID 111,2-Dichloroethane2×HCID 24648Sulfuryl chlorideHCID 159604752-Octyl-1H-1lambda~4~,2-thiazole-1,3(2H)-dione

Product 1

HCID 123182334,5-Dichloro-2-octyl-1lambda~4~,2-thiazolidine-1,3-dione

Procedure

To a solution of 2.29g. (0.01 mole) of 2-n-octyl-4-isothiazolin-3-one 1-oxide in 3 ml. of EDC is added 1.2g. (0.01 mole) of sulfuryl chloride in 3 ml. of EDC. The mixture is stirred at room temperature over a weekend. The solution is filtered and concentrated to give an oil. The oil is further purified via column chromatography (100% benzene: silica) to give 1.0g. (33%) of product.

Workup

  1. filtrationThe solution is filtered
  2. concentrationconcentrated
  3. customto give an oil
  4. customThe oil is further purified via column chromatography (100% benzene: silica)
  5. customto give 1.0g

Sources & evidence

ORD record
ord-3e9c50825294447eb3d815dacd4134a0
Source dataset
uspto-grants-1977_12
Patent number
US04062859

Reaction notes

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