Ammonium formate → HCID 19424416, compound

HRID 743453Notes

Reaction equation

HRID 743453 reaction equation
C1(C[N:8]2[C:12](=[O:13])[C:11]([CH3:17])([CH2:14][CH2:15][CH3:16])[N:10]([CH3:18])[S:9]2(=[O:20])=[O:19])C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[CH3:17][C:11]1([CH2:14][CH2:15][CH3:16])[N:10]([CH3:18])[S:9](=[O:20])(=[O:19])[NH:8][C:12]1=[O:13]

Participants

5

Reactant 2

HCID 2723923Ammonium formate2×HCID 19424429HCID 19424429, compound

Product 1

HCID 19424416HCID 19424416, compoundYield 93.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-phenylmethyl-4-methyl-4-propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (8.78 g, 29.62 mmol) in 250 ml of dry methanol was added 1.5 g of 10% Pd/C followed by ammonium formate (5.6 g, 88.68 mmol), and the mixture was stirred at room temperature for 4 hours. After adding an additional ammonium formate (2×3 equiv), the mixture was heated at 80°-90° C. overnight, cooled, filtered through a pad of CELITE® and the residue was washed with methanol. The combined filtrate was concentrated in vacuo to afford 5.7 g of 4-methyl-4 -propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula IV: R1 =propyl; R2 =CH3 ; R3 =CH3) as a solid.

Workup

  1. temperaturethe mixture was heated at 80°-90° C. overnight
  2. temperaturecooled
  3. filtrationfiltered through a pad of CELITE®
  4. washthe residue was washed with methanol
  5. concentrationThe combined filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-4fcd01886a2440da9bbe832c885b77ba
Source dataset
uspto-grants-1996_09
Patent number
US05556909

Reaction notes

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