Benzyl Bromide → 2-Phenylmethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

HRID 2396782Notes

Reaction equation

HRID 2396782 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([CH2:18]Br)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.CN(C=O)C>[C:12]1([CH2:18][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 7498Benzyl BromideHCID 189222484-Propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

Product 1

HCID 189222572-Phenylmethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxideYield 35.5%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 21735183Dimethylformamide tolueneSolvent

Procedure

A mixture of 4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (20.74 g, 0.117 tool) , phenylmethyl bromide (22.09 g, 0. 129 mol) and tetrabutylammonium bromide (3.77 g, 0. 012 tool) suspended in toluene/DMF (400ml:50ml) was refluxed for 40 hours, and cooled. The mixture was poured into ice/water, extracted with ethyl acetate, and the organic layer was concentrated in vacuo. The residue was purified by flash chromatography to afford 11.1 g of 2-phenylmethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula IX: R1 =H; R2 =propyl) as a solid.

Workup

  1. temperaturewas refluxed for 40 hours
  2. temperaturecooled
  3. extractionextracted with ethyl acetate
  4. concentrationthe organic layer was concentrated in vacuo
  5. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-0399cbb2d8e24764a9ec006a7548e633
Source dataset
uspto-grants-1996_02
Patent number
US05494925

Reaction notes

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