Chloromethyl phenyl sulphide → 2-Phenylthiomethyl-4-propyl-5-ethyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

HRID 743444Notes

Reaction equation

HRID 743444 reaction equation
[CH2:1]([CH:4]1[N:8]([CH2:9][CH3:10])[S:7](=[O:12])(=[O:11])[NH:6][C:5]1=[O:13])[CH2:2][CH3:3].[C:14]1([S:20][CH2:21]Cl)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.CN(C=O)C>[C:14]1([S:20][CH2:21][N:6]2[C:5](=[O:13])[CH:4]([CH2:1][CH2:2][CH3:3])[N:8]([CH2:9][CH3:10])[S:7]2(=[O:12])=[O:11])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 81623Chloromethyl phenyl sulphideHCID 19424396HCID 19424396, compound

Product 1

HCID 194244522-Phenylthiomethyl-4-propyl-5-ethyl-1,2,5-thiadiazolidin-3-one 1,1-dioxideYield 73.5%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 21735183Dimethylformamide tolueneSolvent

Procedure

A mixture of 4-propyl-5-ethyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (3.7 g, 16.6 mmol), phenylthiomethyl chloride (2.9 g, 18.28 mmol) and tetrabutylammonium bromide (0.53 g, 3.1 mmol) suspended in toluene/DMF (90 ml/10 ml) was refluxed for 8 hours, cooled, and concentrated in vacuo. The residue was diluted with water, extracted with ether/ethyl acetate (500 ml, 1:1), and the organic layer was washed with water and brine. The organic layer was dried, concentrated in vacuo, and the residue was purified by flash chromatography to afford 4.01 g of 2-phenylthiomethyl-4-propyl-5-ethyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula VI: R1 =H; R2 =propyl; R3 =ethyl) as an oil.

Workup

  1. temperaturewas refluxed for 8 hours
  2. temperaturecooled
  3. concentrationconcentrated in vacuo
  4. additionThe residue was diluted with water
  5. extractionextracted with ether/ethyl acetate (500 ml, 1:1)
  6. washthe organic layer was washed with water and brine
  7. customThe organic layer was dried
  8. concentrationconcentrated in vacuo
  9. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-506c5f7217b24dd3b558ef635d50bce4
Source dataset
uspto-grants-1996_09
Patent number
US05556909

Reaction notes

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