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

HRID 1450455Notes

Reaction equation

HRID 1450455 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

6

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 35.4%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (20.74 g, 0.117 mol), phenylmethyl bromide (22.09 g, 0.129 mol), and tetrabutylammonium bromide (3.77 g, 0.012 mol) in toluene (400 ml) and DMF (50 ml) was refluxed for 40 hours, cooled, and poured over ice/water. The crude product 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 VII: R1 =propyl; R2 =R3 =H).

Workup

  1. temperaturewas refluxed for 40 hours
  2. temperaturecooled
  3. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-d6f7c18bd563435db4c8d1cc57e1f900
Source dataset
uspto-grants-1997_02
Patent number
US05602154

Reaction notes

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