Sodium hydride → HCID 19870512, compound

HRID 330036Notes

Reaction equation

HRID 330036 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:23]=[N:24][CH:25]=[CH:26][CH:27]=1)[CH2:16][N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1>CN(C)C=O>[N:24]1[CH:25]=[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]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 237573Methyl 4-sulfanylbenzoateHCID 19870535HCID 19870535, compound

Product 1

HCID 19870512HCID 19870512, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

192 mg of a 55% w/w suspension of sodium hydride in mineral oil were added to 4 ml of dry dimethylformamide containing 740 mg of methyl 4-mercaptobenzoate, whilst ice-cooling, and the resulting mixture was stirred at room temperature for 30 minutes. 830 mg of 1-[2-chloro-2-(3-pyridyl)ethyl]imidazole in 4 ml of dry dimethylformamide were added to the reaction mixture, and the resulting mixture was heated at 60°-70° C. for 5 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 615 mg of the title compound as an oil.

Workup

  1. temperaturecooling
  2. temperaturethe resulting mixture was heated at 60°-70° C. for 5 hours
  3. additionAt the end of this time the reaction mixture was treated
  4. custompurified by the same method

Sources & evidence

ORD record
ord-8afa985991ba4eaf8b952d763784c9c3
Source dataset
uspto-grants-1990_01
Patent number
US04894385

Reaction notes

Loading…