Sodium hydride → Methyl 4-[1-(2,4,6-trimethylphenyl)-2-(imidazol-1-yl)ethylthio]benzoate
Reaction equation
[SH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH:15]([C:22]1[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[CH:24][C:23]=1[CH3:30])[CH2:16][N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1>CN(C)C=O>[CH3:28][C:27]1[CH:26]=[C:25]([CH3:29])[CH:24]=[C:23]([CH3:30])[C:22]=1[CH:15]([S:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1)[CH2:16][N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
947 mg of methyl 4-mercaptobenzoate were dissolved in 6 ml of dry dimethylformamide, and 245 mg of a 55% w/w suspension of sodium hydride in mineral oil were added, whilst ice-cooling, to the resulting solution. The mixture was then stirred at room temperature for 30 minutes. 1.4 g of 1-[2-chloro-2-(2,4,6-trimethylphenyl)ethyl]imidazole dissolved in 7 ml of dry dimethylformamide was added to the solution, and the mixture was then heated at 60° to 65° C. for 20 hours. At the end of this time, the resulting mixture was treated and purified similarly to the procedure described in Example 1, to give 1.72 g of the title compound as an oil.
Workup
- additionwere added, whilst ice-
- temperaturecooling, to the resulting solution
- additionwas added to the solution
- temperaturethe mixture was then heated at 60° to 65° C. for 20 hours
- additionAt the end of this time, the resulting mixture was treated
- custompurified similarly to the procedure
Sources & evidence
- ORD record
- ord-2e48d849c35e4e3fb2d8e0cea3f84f2a
- Source dataset
- uspto-grants-1990_01
- Patent number
- US04894385
Reaction notes
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