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

HRID 1736324Notes

Reaction equation

HRID 1736324 reaction equation
[Cs].[CH3:2][CH:3]([CH3:15])[CH2:4][CH2:5][CH:6]1[N:10]([CH3:11])[S:9](=[O:13])(=[O:12])[NH:8][C:7]1=[O:14].[C:16]1([S:22][CH2:23]Cl)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CO.CN(C=O)C>[C:16]1([S:22][CH2:23][N:8]2[C:7](=[O:14])[CH:6]([CH2:5][CH2:4][CH:3]([CH3:15])[CH3:2])[N:10]([CH3:11])[S:9]2(=[O:13])=[O:12])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 81623Chloromethyl phenyl sulphideHCID 867492844-(3-Methylbutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide cesium salt

Product 1

HCID 194244062-Phenylthiomethyl-4-(3-methylbutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxideYield 70.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 4-(3-methylbutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide cesium salt (prepared by reacting 7.7 g (34.95 mmol) of the compound of example 4(g) in methanol with 5.13 g of CS2CO3, followed by removal of the solvent and drying under high vacuum) and phenylthiomethyl chloride (6.65 g, 41.94 mmol) suspended in DMF was heated at 85° C. for 17 hours. The mixture was cooled, and poured into 300 ml of ice/water. The reaction mixture was extracted with ethyl acetate (3×) and the organic layer was washed with water and brine, and dried over sodium sulfate. The organic layer was concentrated in vacuo and the residue was purified by silica column chromatography (10% ethyl acetate in hexane) to afford 8.15 g (70.6%) of 2-phenylthiomethyl-4-(3-methylbutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula VI: R1 =H; R2 =(CH2)2CH(CH3)2 ; R3 =CH3) as a solid.

Workup

  1. customprepared
  2. customfollowed by removal of the solvent
  3. temperatureThe mixture was cooled
  4. extractionThe reaction mixture was extracted with ethyl acetate (3×)
  5. washthe organic layer was washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. concentrationThe organic layer was concentrated in vacuo
  8. customthe residue was purified by silica column chromatography (10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-8633513babdd4d5981ded7079f39ed22
Source dataset
uspto-grants-1996_07
Patent number
US05541168

Reaction notes

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