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]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.CI.[Cl-].[NH4+]>C1COCC1>[C:7]1([CH2:13][N:14]2[C:18](=[O:19])[CH:17]([CH2:20][CH2:21][CH3:22])[N:16]([CH3:1])[S:15]2(=[O:23])=[O:24])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Potassium t-butoxide (1.83 g, 14.9 mmol) was added to a solution of 2-phenylmethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (4 g, 14.9 mmol) in 150 ml of THF at 0° C. and the mixture was stirred for 1 hour at the same temperature. To the above mixture was added 10.58 g (74.6 mmol) of methyl iodide, and the reaction mixture was stirred at 0° C. for 0.5 hour, at room temperature for 6 hours, and decomposed with saturated ammonium chloride solution. The resulting mixture was extracted with methylene chloride and the organic layer was washed with brine, dried, and concentrated in vacuo to afford 4.19 g (quantitative) of 2-phenylmethyl-5-methyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula IX: R1 =propyl; R2 =H; R3 =CH3).
Workup
- stirringthe reaction mixture was stirred at 0° C. for 0.5 hour, at room temperature for 6 hours
- extractionThe resulting mixture was extracted with methylene chloride
- washthe organic layer was washed with brine
- customdried
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-3a0b680adb3045739360045b0a8f1ce8
- Source dataset
- uspto-grants-1998_05
- Patent number
- US05750546
Reaction notes
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