Sodium hydride → HCID 19870526, compound

HRID 330020Notes

Reaction equation

HRID 330020 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]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[C:24]([O:32][CH3:33])[CH:23]=1)[CH2:16][N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1>CN(C)C=O>[CH3:33][O:32][C:24]1[CH:23]=[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:27]=[C:26]([O:28][CH3:29])[C:25]=1[O:30][CH3:31]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 237573Methyl 4-sulfanylbenzoateHCID 19870537HCID 19870537, compound

Product 1

HCID 19870526HCID 19870526, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

48.5 mg of a 55% w/w suspension of sodium hydride in mineral oil were added, whilst ice-cooling, to a solution of 187 mg of methyl 4-mercaptobenzoate in 1.3 ml of dry dimethylformamide, and the reaction mixture was then stirred at room temperature for 30 minutes. To this solution was added 1.3 ml of dry dimethylformamide containing 330 mg of 1-[2-chloro-2-(3,4,5-trimethoxyphenyl)ethyl]imidazole, and the reaction mixture was heated at 60°-70° C. for 7.5 hours. At the end of this time, the resulting mixture was treated and purified by the same method as described in Example 1, to give 187.7 mg of the title compound as an oil.

Workup

  1. additionwere added, whilst ice-
  2. temperaturethe reaction mixture was heated at 60°-70° C. for 7.5 hours
  3. additionAt the end of this time, the resulting mixture was treated
  4. custompurified by the same method

Sources & evidence

ORD record
ord-6e7141563083422cb667787012205b99
Source dataset
uspto-grants-1990_01
Patent number
US04894385

Reaction notes

Loading…