Sodium hydride → HCID 19870529, compound

HRID 330018Notes

Reaction equation

HRID 330018 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]([CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)[CH2:16][N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1>CN(C)C=O>[CH:22]1([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)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 237573Methyl 4-sulfanylbenzoateHCID 19870508HCID 19870508, compound

Product 1

HCID 19870529HCID 19870529, compoundYield 53.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

779 mg of a 55% w/w suspension of sodium hydride in mineral oil were added to a solution of 3 g of methyl 4-mercaptobenzoate in 24 ml of dry dimethylformamide, and the resulting mixture was stirred at room temperature for 30 minutes. A solution of 3.8 g of 1-(2-chloro-2-cyclohexylethyl)imidazole in 36 ml of dry dimethylformamide was added to the resulting solution, and the reaction mixture was then heated at 60°-70° C. for 13.5 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 3.3 g of the title compound as an oil.

Workup

  1. temperaturethe reaction mixture was then heated at 60°-70° C. for 13.5 hours
  2. additionAt the end of this time, the resulting mixture was treated
  3. custompurified by the same method

Sources & evidence

ORD record
ord-cddbaddc27ef49b6945bea8f729f9d1f
Source dataset
uspto-grants-1990_01
Patent number
US04894385

Reaction notes

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