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

HRID 1450457Notes

Reaction equation

HRID 1450457 reaction equation
C1(C[N:8]2[C:12](=[O:13])[CH:11]([CH2:14][CH2:15][CH3:16])[N:10]([CH3:17])[S:9]2(=[O:19])=[O:18])C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].CO>[CH3:17][N:10]1[S:9](=[O:19])(=[O:18])[NH:8][C:12](=[O:13])[CH:11]1[CH2:14][CH2:15][CH3:16]

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 81.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-phenylmethyl-5-methyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (4.15 g ), 10% Pd/C (2.0 g), and ammonium formate (8.0 g) and methanol was stirred overnight at room temperature. The solvent was removed and the crude product was purified by flash chromatography to afford 2.3 g (80.9%) of 5-methyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula IV: R1 =propyl; R2 =H; R3 =CH3).

Workup

  1. customThe solvent was removed
  2. customthe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-6df272dcf8944c8998da7d3263181f8c
Source dataset
uspto-grants-1997_02
Patent number
US05602154

Reaction notes

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