Methyl iodide → HCID 19424429, compound

HRID 743452Notes

Reaction equation

HRID 743452 reaction equation
[CH3:1]C(C)([O-])C.[K+].[C:7]1([CH2:13][N:14]2[C:18](=[O:19])[C:17]([CH3:23])([CH2:20][CH2:21][CH3:22])[NH:16][S:15]2(=[O:25])=[O:24])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CI.[Cl-].[NH4+]>C1COCC1>[C:7]1([CH2:13][N:14]2[C:18](=[O:19])[C:17]([CH3:23])([CH2:20][CH2:21][CH3:22])[N:16]([CH3:1])[S:15]2(=[O:24])=[O:25])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 19424440HCID 19424440, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 19424429HCID 19424429, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium t-butoxide (3.93 g, 35.06 mmol) was added in one portion to a solution of 2-phenylmethyl-4-methyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (9 g, 31.87 mmol) in 250 ml of THF at 0° C. and the mixture was stirred under nitrogen at this temperature for 1 hour. To the mixture was added methyl iodide (27.14 g, 191.22 mmol) at 0° C. and the resulting mixture was allowed to stir at 0° C. for 1/2 hour and at room temperature for 11 hours. The resulting mixture was poured into 400 ml of saturated ammonium chloride solution, extracted with ethyl acetate, and the organic layer was washed with water and brine. The organic layer was dried over sodium sulfate, concentrated in vacuo to afford 9.28 g (98%) of 2-phenylmethyl-4-methyl-4 -propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula XI: R1 =propyl; R2 =CH3 ; R3 =methyl ) as an oil.

Workup

  1. stirringto stir at 0° C. for 1/2 hour and at room temperature for 11 hours
  2. extractionextracted with ethyl acetate
  3. washthe organic layer was washed with water and brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8332a62a714d4f7fbb5bfe6deab5c33e
Source dataset
uspto-grants-1996_09
Patent number
US05556909

Reaction notes

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