Sodium hydride → 1,4-Dimethyl-2-(4-methoxybenzylthio)-5-[2-(methylsulfinyl)-2-(methylthio)ethenyl]imidazole
Reaction equation
[CH3:1][N:2]1[C:6]([CH:7]=O)=[C:5]([CH3:9])[N:4]=[C:3]1[S:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1.[H-].[Na+].C[CH:23]([S:27][CH:28](S(C)=O)C)[S:24]([CH3:26])=[O:25]>O1CCCC1>[CH3:1][N:2]1[C:6]([CH:7]=[C:23]([S:24]([CH3:26])=[O:25])[S:27][CH3:28])=[C:5]([CH3:9])[N:4]=[C:3]1[S:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
1,4-Dimethyl-5-formyl-2-(4-methoxybenzylthio)imidazole (8 g, 0.03 mole) in tetrahydrofuran (30 ml) was added to a mixture prepared by adding sodium hydride (1.8 g, 38 mmoles) to a solution of methyl methylsulfinylmethylsulfide (4.7 g, 38 mmoles) in tetrahydrofuran. The mixture was stirred for 16 hours, concentrated in vacuo and the residue was partitioned between water and methylene chloride. The organic phase was dried with sodium sulfate, concentrated in vacuo and the residue chromatographed on silica gel eluted with ethyl acetate to give 1,4-dimethyl-2-(4-methoxybenzylthio)-5-[2-(methylsulfinyl)-2-(methylthio)ethenyl]imidazole.
Workup
- customprepared
- concentrationconcentrated in vacuo
- customthe residue was partitioned between water and methylene chloride
- dry with materialThe organic phase was dried with sodium sulfate
- concentrationconcentrated in vacuo
- customthe residue chromatographed on silica gel
- washeluted with ethyl acetate
Sources & evidence
- ORD record
- ord-c436c1b997534d30b83ff7fc79da1253
- Source dataset
- uspto-grants-1988_09
- Patent number
- US04769386
Reaction notes
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