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

HRID 1736318Notes

Reaction equation

HRID 1736318 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 627.4%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

To a mixture of 4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (5.1 g, 28.65 mmol) suspended in 210 ml of toluene was added tetrabutylammonium bromide (0.92 g, 2.86 mmol) and phenylthiomethyl chloride (4.93 g, 2.86 mmol) and the resulting mixture was refluxed for 18 hours. The mixture was cooled, filtered, and the filtrate was concentrated in vacuo. The residue was purified by silica gel flash column chromatography (20% ethyl acetate in hexane) to afford 5.39 g (63%) 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 resulting mixture was refluxed for 18 hours
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified by silica gel flash column chromatography (20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-9725a8db1020453999eac617ebbf0ca2
Source dataset
uspto-grants-1996_07
Patent number
US05541168

Reaction notes

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