Sodium hydride → HCID 19870514, compound

HRID 330007Notes

Reaction equation

HRID 330007 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[S:23][CH:24]=[CH:25][CH:26]=1)[CH2:16][N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1>CN(C)C=O>[S:23]1[CH:24]=[CH:25][CH:26]=[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]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 237573Methyl 4-sulfanylbenzoateHCID 19870532HCID 19870532, compound

Product 1

HCID 19870514HCID 19870514, compoundYield 4.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

204 mg of methyl 4-mercaptobenzoate were dissolved in 1.3 ml of dry dimethylformamide, and 53 mg of a 55% w/w suspension of sodium hydride in mineral oil were added to the resulting solution, whilst ice-cooling. The mixture was then stirred at room temperature for 30 minutes. 258 mg of 1-[2-chloro-2-(2-thienyl)ethyl]imidazole dissolved in 1.3 ml of dry dimethylformamide were added to the resulting solution, and the mixture was then heated at 60° to 70° C. for 8 hours. At the end of this time, the resulting mixture was treated and purified similarly to the procedure described in Example 1, to give 20 mg of the title compound as an oil.

Workup

  1. additionwere added to the resulting solution, whilst ice-
  2. temperaturecooling
  3. additionwere added to the resulting solution
  4. temperaturethe mixture was then heated at 60° to 70° C. for 8 hours
  5. additionAt the end of this time, the resulting mixture was treated
  6. custompurified similarly to the procedure

Sources & evidence

ORD record
ord-0d17749b6f8b4c3cba221b9592cb185e
Source dataset
uspto-grants-1990_01
Patent number
US04894385

Reaction notes

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