Sodium hydride → HCID 19870510, compound

HRID 330016Notes

Reaction equation

HRID 330016 reaction equation
[SH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH:15]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[Cl:28])[CH2:16][N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1>CN(C)C=O>[Cl:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[CH:15]([S:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1)[CH2:16][N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 237573Methyl 4-sulfanylbenzoateHCID 19870536HCID 19870536, compound

Product 1

HCID 19870510HCID 19870510, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

6.4 g of methyl 4-mercaptobenzoate were dissolved in 45 ml of dry dimethylformamide, and 1.7 g of a 55% w/w suspension of sodium hydride in mineral oil was added to the resulting solution, whilst ice-cooling. The resulting mixture was then stirred at room temperature for 30 minutes, after which a solution of 9.2 g of 1-[2-chloro-2-(2-chlorophenyl)ethyl]imidazole in 45 ml of dry dimethylformamide was added to the resulting solution, and the reaction mixture was heated at 50° C. for 6.5 hours. At the end of this time, the resulting solution was treated and purified in a similar manner to that described in Example 1, to give 8.08 g of the title compound as an oil.

Workup

  1. additionwas added to the resulting solution, whilst ice-
  2. temperaturecooling
  3. temperaturethe reaction mixture was heated at 50° C. for 6.5 hours
  4. additionAt the end of this time, the resulting solution was treated
  5. custompurified in a similar manner to that

Sources & evidence

ORD record
ord-b97b025a026d41a6abc384eecd7d0c95
Source dataset
uspto-grants-1990_01
Patent number
US04894385

Reaction notes

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