Ammonium formate → 4-Propyl-5-ethyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide ammonium salt

HRID 743443Notes

Reaction equation

HRID 743443 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]([CH2:21][CH3:22])[S:13]2(=[O:24])=[O:23])C=CC=CC=1>CO.[Pd]>[NH4+:12].[CH2:18]([CH:15]1[N:14]([CH2:21][CH3:22])[S:13](=[O:24])(=[O:23])[NH:12][C:16]1=[O:17])[CH2:19][CH3:20]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 194244172-Phenylmethyl-4-propyl-5-ethyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

Product 1

HCID 194243954-Propyl-5-ethyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide ammonium saltYield 191.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2 g of 10% Pd/C, ammonium formate (3.35 g), and 2-phenylmethyl-4-propyl-5-ethyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (5.25 g) in 300 ml of methanol was stirred at room temperature for 20 hours, filtered through a pad of CELITE®, and the residue was washed with methanol. The combined filtrate was concentrated in vacuo to afford 3.8 g of 4-propyl-5-ethyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide ammonium salt (Formula IV: R1 =H; R2 =propyl; R3 =ethyl; as NH4+ salt) 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-b9fcb2a809e14daa9ed358e16ec51642
Source dataset
uspto-grants-1996_09
Patent number
US05556909

Reaction notes

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