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

HRID 743434Notes

Reaction equation

HRID 743434 reaction equation
[CH2:1]([CH:4]1[N:8]([CH3:9])[S:7](=[O:11])(=[O:10])[NH:6][C:5]1=[O:12])[CH2:2][CH3:3].[C:13]1([S:19][CH2:20]Cl)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[C:13]1([S:19][CH2:20][N:6]2[C:5](=[O:12])[CH:4]([CH2:1][CH2:2][CH3:3])[N:8]([CH3:9])[S:7]2(=[O:11])=[O:10])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 81623Chloromethyl phenyl sulphideHCID 189222534-Propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

Product 1

HCID 194244492-Phenylthiomethyl-4-propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxideYield 88%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 4-propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (9 g), phenylthiomethyl chloride (7.43 g) and tetrabutylammonium bromide (1 g) suspended in 200 ml of toluene was refluxed for 8 hours, cooled, and concentrated in vacuo. The residue was purified by flash chromatography (15%-20% ethyl acetate in hexane) to afford 8.5 g (88%) of 2-phenylthiomethyl-4-propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula VI: R1 =H; R2 =propyl; R3 =methyl).

Workup

  1. temperaturewas refluxed for 8 hours
  2. temperaturecooled
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography (15%-20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-bc4a52da484f481195bf311c721d48cd
Source dataset
uspto-grants-1996_09
Patent number
US05556909

Reaction notes

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