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

HRID 743439Notes

Reaction equation

HRID 743439 reaction equation
[CH:1]([O-:3])=O.[NH4+].[C:5]1([CH2:11][N:12]2[C:16](=O)C(C(C)C)[N:14](C)[S:13]2(=[O:23])=[O:22])C=CC=[CH:7][CH:6]=1>CO.[Pd]>[CH2:5]([CH:11]1[N:12]([CH3:16])[S:13](=[O:23])(=[O:22])[NH:14][C:1]1=[O:3])[CH2:6][CH3:7]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 194244432-Phenylmethyl-4-isopropyl-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-dioxide

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 (15 g) was added a solution of 2-phenylmethyl-4-isopropyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (7.1 g) in 50 ml of methanol under nitrogen. The mixture was stirred at room temperature for 7 hours, filtered through a pad of CELITE® and the residue was washed with methanol. The combined filtrate was concentrated in vacuo to afford 4-isopropyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide 2-ammonium salt (Formula IV: R1 =H; R2 =isopropyl; R3 =methyl; as NH4+ salt).

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-fb1aa869e59f438292ad5ae9d905de83
Source dataset
uspto-grants-1996_09
Patent number
US05556909

Reaction notes

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