Methyl iodide → HCID 19424431, compound

HRID 743471Notes

Reaction equation

HRID 743471 reaction equation
[CH3:1]C(C)([O-])C.[K+].[C:7]1([S:13][CH2:14][N:15]2[C:19](=[O:20])[CH:18]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[NH:17][S:16]2(=[O:29])=[O:28])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CI>C1COCC1>[C:7]1([S:13][CH2:14][N:15]2[C:19](=[O:20])[CH:18]([CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:17]([CH3:1])[S:16]2(=[O:28])=[O:29])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 19424441HCID 19424441, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 19424431HCID 19424431, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium t-butoxide (5.65 g, 50.35 mmol) was added to a solution of 2-phenylthiomethyl-4-phenylmethyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (14.61 g, 41.93 mmol) in 250 ml of THF at 0° C. and the mixture was stirred at this temperature for 1/2 hour. To the above mixture was added methyl iodide (35.69 g, 251.58 mmol) at 0° C. and the resulting mixture was allowed to stir for 4.5 hours at room temperature. The resulting mixture was quenched with saturated ammonium chloride solution, extracted with ethyl acetate 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 12.53 g (82.4%) of 2-phenylthiomethyl-4-phenylmethyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide as a yellow solid.

Workup

  1. stirringto stir for 4.5 hours at room temperature
  2. customThe resulting mixture was quenched with saturated ammonium chloride solution
  3. extractionextracted with ethyl acetate
  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-5c58623a43824524a1dbda757851569e
Source dataset
uspto-grants-1996_09
Patent number
US05556909

Reaction notes

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