Sodium hydride → HCID 19870520, compound

HRID 330022Notes

Reaction equation

HRID 330022 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][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=1)[CH2:16][N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1>CN(C)C=O>[CH3:29][O:28][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]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 237573Methyl 4-sulfanylbenzoateHCID 19870525HCID 19870525, compound

Product 1

HCID 19870520HCID 19870520, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

144 mg of a 55% w/w suspension of sodium hydride in mineral oil were added, whilst ice-cooling, to a solution of 555 mg of methyl 4-mercaptobenzoate in 4 ml of dry dimethylformamide, and the resulting mixture was stirred at room temperature for 30 minutes. A solution of 710 of 1-[2-chloro-2-(3-methoxyphenyl)ethyl]imidazole in 3 ml of dry dimethylformamide was added to this solution, and the reaction mixture was heated at 60°-70° C. for 5.5 hours. At the end of this time, the resulting mixture was treated and purified according to the same procedure as described in Example 1, to give 631 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 5.5 hours
  3. additionAt the end of this time, the resulting mixture was treated
  4. custompurified

Sources & evidence

ORD record
ord-5d60e3d6967d4e2ebfac0b2b01f0bde9
Source dataset
uspto-grants-1990_01
Patent number
US04894385

Reaction notes

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