Ammonium formate → 4-Propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

HRID 2396774Notes

Reaction equation

HRID 2396774 reaction equation
C([O-])=O.[NH4+].C1(C[N:12]2[C:16](=[O:17])[CH:15]([CH2:18][CH2:19][CH3:20])[N:14]([CH3:21])[S:13]2(=[O:23])=[O:22])C=CC=CC=1>CO.[Pd]>[CH2:18]([CH:15]1[N:14]([CH3:21])[S:13](=[O:23])(=[O:22])[NH:12][C:16]1=[O:17])[CH2:19][CH3:20]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 189222542-Phenylmethyl-4-propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

Product 1

HCID 189222534-Propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxideYield 128.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

To a suspension of 3.5 g of 10% Pd/C in 150 ml of methanol containing ammonium formate (14 g) was added a solution of 2-phenylmethyl-4-propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (8.7 g) in 40 ml of methanol under nitrogen. The mixture was stirred at room temperature for 15 hours, filtered through a pad of CELITE® and the residue was washed with methanol. The combined filtrate was concentrated in vacuo to afford 7.6 g of 4-propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula IV: R1 =H; R2 =propyl; R3 =CH3) as a solid.

Workup

  1. filtrationfiltered through a pad of CELITE®
  2. washthe residue was washed with methanol
  3. concentrationThe combined filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-5b68918cca73463dbbd3a4206312e92d
Source dataset
uspto-grants-1996_02
Patent number
US05494925

Reaction notes

Loading…