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

HRID 2396765Notes

Reaction equation

HRID 2396765 reaction equation
[CH2:1]([CH:4]1[NH:8][S:7](=[O:10])(=[O:9])[NH:6][C:5]1=[O:11])[CH2:2][CH3:3].[C:12]1([S:18][CH2:19]Cl)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:12]1([S:18][CH2:19][N:6]2[C:5](=[O:11])[CH:4]([CH2:1][CH2:2][CH3:3])[NH:8][S:7]2(=[O:9])=[O:10])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 81623Chloromethyl phenyl sulphideHCID 189222484-Propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

Product 1

HCID 194244652-Phenylthiomethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxideYield 69%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a mixture of 4-propyl-1,2,5-thiadiazolidin-3-one 1,1dioxide (1.0 g, 5.6 mmol) suspended in 15 ml of toluene containing tetrabutylammonium bromide (0.18 g, 0.56 mmol) was added phenylthiomethyl chloride (0.98 g, 6.2 mmol) and the resulting mixture was refluxed (120° C.) for 20 hours. The mixture was cooled, filtered, and the filtrate was concentrated in vacuo. The residue was purified by silica gel flash column chromatography (20% of ethyl acetate in hexane) to afford 1.16 g of 2-phenylthiomethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula VI: R1 =H; R2 =propyl; R3 =H).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by silica gel flash column chromatography (20% of ethyl acetate in hexane)

Sources & evidence

ORD record
ord-facc736e09334ab9856067b16e437fc2
Source dataset
uspto-grants-1996_02
Patent number
US05494925

Reaction notes

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