Methyl iodide → 2-Phenylmethyl-4-propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide
Reaction equation
[CH3:1]C(C)([O-])C.[K+].[C:7]1([CH2:13][N:14]2C(=O)[CH:17](C(C)C)[NH:16][S:15]2(=[O:24])=[O:23])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CI.[CH2:27]1[CH2:31][O:30][CH2:29][CH2:28]1>>[C:7]1([CH2:13][N:14]2[C:29](=[O:30])[CH:28]([CH2:27][CH2:31][CH3:1])[N:16]([CH3:17])[S:15]2(=[O:24])=[O:23])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1Participants
Procedure
To a solution of potassium t-butoxide (3.53 g, 29 mmol) in THF was added a solution of 2-phenylmethyl-4-isopropyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (7.7 g, 29 mmol) 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 =methyl) as a solid, m.p. 52.5°-54° C.
Workup
- stirringto stir at room temperature for 2.5 hours
- customThe resulting mixture was quenched with brine
- extractionextracted with ether
- washthe organic layer was washed with brine
- customThe organic layer was dried
- concentrationconcentrated in vacuo
- customthe residue was purified by flash chromatography
Sources & evidence
- ORD record
- ord-4836984d84a2415785cf7a69a7effcb2
- Source dataset
- uspto-grants-1996_09
- Patent number
- US05556909
Reaction notes
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