Toluene → 2-Phenylthiomethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

HRID 2396771Notes

Reaction equation

HRID 2396771 reaction equation
[CH:1]([CH:4]1[NH:8][S:7](=[O:10])(=[O:9])[NH:6][C:5]1=[O:11])(C)[CH3:2].[C:12]1([S:18][CH2:19]Cl)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[C:21]1(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][CH3:21])[NH:8][S:7]2(=[O:10])=[O:9])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 81623Chloromethyl phenyl sulphideHCID 194244514-Isopropyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

Product 1

HCID 194244652-Phenylthiomethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Procedure

To a mixture of 4-isopropyl-1,2, 5-thiadiazolidin-3-one 1, 1-dioxide (7.0 g, 39.32 retool) suspended in 150 ml of toluene was added phenylthiomethyl chloride (6.83 g, 43 mmol) and tetrabutylammonium bromide (1.26 g, 3.93 retool). The resulting mixture was refluxed for 17 hours, cooled, filtered, and the filtrate was concentrated in vacuo. The residue was purified by column chromatography to afford 5.2 g of 2-phenylthiomethyl-4-isopropyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula VI: R1 =H; R2 =isopropyl; R3 =H) .

Workup

  1. temperatureThe resulting mixture was refluxed for 17 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-d863fc26596d458b8650799e2497cdad
Source dataset
uspto-grants-1996_02
Patent number
US05494925

Reaction notes

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