Methyl iodide → 2-(2-Isopropylphenyl)imino-3-(methylthio)thiocarbonyl-1,3-thiazolidine
Reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]=[C:11]1[NH:15][CH2:14][CH2:13][S:12]1)([CH3:3])[CH3:2].[C:16](=[S:18])=[S:17].[H-].[Na+].[CH3:21]I>O.CN(C)C=O>[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]=[C:11]1[N:15]([C:16]([S:18][CH3:21])=[S:17])[CH2:14][CH2:13][S:12]1)([CH3:3])[CH3:2]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a mixture of 2-(2-isopropylphenyl)imino-1,3-thiazolidine (0.22 g), carbon disulfide (0.09 g) and N,N-dimethylformamide (2 ml) was added under ice-cooling 60% sodium hydride (0.05 g). The mixture was stirred for 30 minutes. Methyliodide (0.17 g) was added thereto. The mixture was stirred at room temperature for 2 hours. To the mixture was added water (30 ml). The mixture was extracted with diethylether (60 ml), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to give 2-(2-isopropylphenyl)imino-3-(methylthio)thiocarbonyl-1,3-thiazolidine (0.14 g, yield: 45%) as colorless oil.
Workup
- additionwas added under ice-
- stirringThe mixture was stirred at room temperature for 2 hours
- extractionThe mixture was extracted with diethylether (60 ml)
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-d75e5dd79e994115aad8e8929f037ceb
- Source dataset
- uspto-grants-2007_02
- Patent number
- US07183275B2
Reaction notes
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