Sodium hydride → HCID 19870505, compound

HRID 330027Notes

Reaction equation

HRID 330027 reaction equation
[H-].[Na+].[SH:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1.Cl[CH:15]([C:22]1[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=1)[CH2:16][N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1>CN(C)C=O>[F:31][C:28]([F:29])([F:30])[C:25]1[CH:26]=[CH:27][C:22]([CH:15]([S:3][C:4]2[CH:5]=[CH:6][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:12][CH:13]=2)[CH2:16][N:17]2[CH:21]=[CH:20][N:19]=[CH:18]2)=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 237573Methyl 4-sulfanylbenzoateHCID 19870527HCID 19870527, compound

Product 1

HCID 19870505HCID 19870505, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

292 mg of a 55% w/w suspension of sodium hydride in mineral oil were added to 1.13 g of methyl 4-mercaptobenzoate in 8 ml of dry dimethylformamide, whilst ice-cooling, and the resulting mixture was stirred at room temperature for 30 minutes. 1.61 g of 1-[2-chloro-2-(4-trifluoromethylphenyl)ethyl]imidazole in 7 ml of dry dimethylformamide was added to this solution and the resulting mixture was heated at 60°-70° C. for 6 hours. At the end of this time, the reaction mixture was treated and purified by the same method as described in Example 1, to give 844 mg of the title compound as an oil.

Workup

  1. temperaturecooling
  2. temperaturethe resulting mixture was heated at 60°-70° C. for 6 hours
  3. additionAt the end of this time, the reaction mixture was treated
  4. custompurified by the same method

Sources & evidence

ORD record
ord-e7261a21c760424399f86bf3366eec6e
Source dataset
uspto-grants-1990_01
Patent number
US04894385

Reaction notes

Loading…