Methyl iodide → 2-Phenylmethyl-4-isopropyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

HRID 2396777Notes

Reaction equation

HRID 2396777 reaction equation
[CH3:1]C(C)([O-])C.[K+].[C:7]1([CH2:13][N:14]2[C:18](=[O:19])[CH:17]([CH:20]([CH3:22])[CH3:21])[NH:16][S:15]2(=[O:24])=[O:23])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CI>C1COCC1>[C:7]1([CH2:13][N:14]2[C:18](=[O:19])[CH:17]([CH:20]([CH3:21])[CH3:22])[N:16]([CH3:1])[S:15]2(=[O:23])=[O:24])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 542672972-Phenylmethyl-4-isopropyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

Product 1

HCID 194244432-Phenylmethyl-4-isopropyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxideYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of potassium t-butoxide (3.53 g, 29 mmol) in THF was added to a solution of 2-phenylmethyl-4-isopropyl-1, 2,5-thiadiazolidin-3-one 1,1-dioxide (7.7 g, 29 retool) in THF at 0° C. and the mixture was stirred at this temperature for 1 hour. To the mixture was added methyl iodide (20.38 g, 0.143 mol) and the resulting mixture was allowed to stir at room temperature for 2.5 hours. The resulting mixture was quenched with brine, extracted with ether, 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 7.1 g (88%) of 2-phenylmethyl-4-isopropyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula XI: R1 =H; R2 =isopropyl; R3 =CH3) as a solid, m.p. 52.5°-54° C.

Workup

  1. stirringto stir at room temperature for 2.5 hours
  2. customThe resulting mixture was quenched with brine
  3. extractionextracted with ether
  4. washthe organic layer was washed with brine
  5. customThe organic layer was dried
  6. concentrationconcentrated in vacuo
  7. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-f630f4aadd7b4746ad0e7d59975128cd
Source dataset
uspto-grants-1996_02
Patent number
US05494925

Reaction notes

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