Methyl iodide → 1-N-methyl-2-(2-dimethylaminobenzylthio)-4,4-dimethyl-2-imidazolin-5-one
Reaction equation
[CH3:1][N:2]([CH3:19])[C:3]1[CH:18]=[CH:17][CH:16]=[CH:15][C:4]=1[CH2:5][S:6][C:7]1[NH:8][C:9]([CH3:14])([CH3:13])[C:10](=[O:12])[N:11]=1.[H-].[Na+].CI.[C:24](OCC)(=O)C>CN(C)C=O.O>[CH3:24][N:11]1[C:10](=[O:12])[C:9]([CH3:14])([CH3:13])[N:8]=[C:7]1[S:6][CH2:5][C:4]1[CH:15]=[CH:16][CH:17]=[CH:18][C:3]=1[N:2]([CH3:1])[CH3:19]Participants
Procedure
To a solution of 0.5 g of 2-(2-dimethylaminobenzylthio)-5,5-dimethylimidazolin-4-one in 20 mL of N,N-dimethylformamide, there was added 60% sodium hydride in 0.09 g of mineral oil at -10° C. After the mixture was stirred for 15 minutes, 1 mL of methyl iodide was added to the mixture, and the stirring was continued for one hour. To the reaction mixture, there were added 100 mL of ethyl acetate (AcOEt) and 100 mL of water. The AcOEt layer was separated. The separated AcOEt layer was washed three times with 50 mL of brine, dried over magnesium sulfate (MgSO4), and concentrated in vacuo. The residue was purified by column chromatography (using CHCl3 as a developing solvent), to give the desired compound in the form of a syrup. The yield of this compound was 0.41 g with a yield ratio of 78.1%.
Workup
- waitthe stirring was continued for one hour
- customThe AcOEt layer was separated
- washThe separated AcOEt layer was washed three times with 50 mL of brine
- dry with materialdried over magnesium sulfate (MgSO4)
- concentrationconcentrated in vacuo
- customThe residue was purified by column chromatography (
Sources & evidence
- ORD record
- ord-a413f39439cd436fae92766aebf207f9
- Source dataset
- uspto-grants-1998_03
- Patent number
- US05733922
Reaction notes
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