Chloromethyl phenyl sulphide → HCID 19424439, compound

HRID 743454Notes

Reaction equation

HRID 743454 reaction equation
[CH3:1][C:2]1([CH2:11][CH2:12][CH3:13])[N:6]([CH3:7])[S:5](=[O:9])(=[O:8])[NH:4][C:3]1=[O:10].[C:14]1([S:20][CH2:21]Cl)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[C:14]1([S:20][CH2:21][N:4]2[C:3](=[O:10])[C:2]([CH3:1])([CH2:11][CH2:12][CH3:13])[N:6]([CH3:7])[S:5]2(=[O:9])=[O:8])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 81623Chloromethyl phenyl sulphideHCID 19424416HCID 19424416, compound

Product 1

HCID 19424439HCID 19424439, compoundYield 17.7%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 4-methyl-4-propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (5.44 g, 28.31 mmol), phenylthiomethyl chloride (5.39 g, 33.97 mmol) and tetrabutylammonium bromide (0. 912 g, 2.83 mmol) suspended in DMF (120 ml) was heated at 75° C. for 23 hours, cooled, and poured into 250 ml of ice/water. The mixture was extracted with ethyl acetate (3×150 ml), and the organic layer was washed with water and brine. The organic layer was dried, concentrated in vacuo, and the residue was purified by flash chromatography (silica gel; 10% ethyl acetate in hexane) to afford 1.65 g (17.7%) of 2-phenylthiomethyl-4-methyl-4-propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula VI: R1 =propyl; R2 =CH3 ; R3 =CH3).

Workup

  1. temperaturecooled
  2. extractionThe mixture was extracted with ethyl acetate (3×150 ml)
  3. washthe organic layer was washed with water and brine
  4. customThe organic layer was dried
  5. concentrationconcentrated in vacuo
  6. customthe residue was purified by flash chromatography (silica gel; 10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-19ec837da11046a182c722ea24961198
Source dataset
uspto-grants-1996_09
Patent number
US05556909

Reaction notes

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