Iodoethane → 2-Phenylmethyl-4-propyl-5-ethyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

HRID 2396783Notes

Reaction equation

HRID 2396783 reaction equation
[CH3:1][C:2](C)([O-])C.[K+].[C:7]1([CH2:13][N:14]2[C:18](=[O:19])[CH:17]([CH2:20][CH2:21][CH3:22])[NH:16][S:15]2(=[O:24])=[O:23])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(I)C>C1COCC1.[Cl-].[Na+].O>[C:7]1([CH2:13][N:14]2[C:18](=[O:19])[CH:17]([CH2:20][CH2:21][CH3:22])[N:16]([CH2:1][CH3:2])[S:15]2(=[O:23])=[O:24])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 189222572-Phenylmethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxideHCID 23665647Potassium tert-butoxide

Product 1

HCID 194244172-Phenylmethyl-4-propyl-5-ethyl-1,2,5-thiadiazolidin-3-one 1,1-dioxideYield 95.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Potassium t-butoxide (2 . 3 g, 20.5 mmol) was added to a solution of 2-phenylmethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1, 1-dioxide (5 g, 18.6 mmol) in 100 ml of THF at 0° C. and the mixture was stirred at this temperature for 1 hour. To the mixture was added ethyl iodide (11.64 g, 74.6 mmol) and the resulting mixture was allowed to stir at room temperature for 40 hours. The resulting mixture was diluted with brine, extracted with ethyl acetate (150 ml) and the organic layer was washed with brine. The organic layer was dried, concentrated in vacuo, and the residue was purified by flash chromatography to afford 5.27 g of 2-phenylmethyl-4-propyl-5-ethyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula XI: R1 =H; R2 =propyl; R3 =ethyl) as an oil.

Workup

  1. stirringto stir at room temperature for 40 hours
  2. extractionextracted with ethyl acetate (150 ml)
  3. washthe organic layer was washed with brine
  4. customThe organic layer was dried
  5. concentrationconcentrated in vacuo
  6. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-7e9a107966eb4c6da8e77de57a65d1fa
Source dataset
uspto-grants-1996_02
Patent number
US05494925

Reaction notes

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