Sodium hydride → HCID 19870509, compound

HRID 330006Notes

Reaction equation

HRID 330006 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][C:25]([F:28])=[CH:24][CH:23]=1)[CH2:16][N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1>CN(C)C=O>[F:28][C:25]1[CH:26]=[CH:27][C:22]([CH:15]([S:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=2)[CH2:16][N:17]2[CH:21]=[CH:20][N:19]=[CH:18]2)=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 237573Methyl 4-sulfanylbenzoateHCID 19870521HCID 19870521, compound

Product 1

HCID 19870509HCID 19870509, compoundYield 49.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

965 mg of methyl 4-mercaptobenzoate were dissolved in 6 ml of dry dimethylformamide. 250 mg of a 55% w/w suspension of sodium hydride in mineral oil were added to the resulting solution, whilst ice-cooling, and the mixture was then stirred at room temperature for 30 minutes. A solution of 1.1 g of 1-[2-chloro-2-(4-fluorophenyl)ethyl]imidazole dissolved in 16 ml of dry dimethylformamide was added to the resulting mixture. The mixture was then heated at 70° to 75° C. for 2.5 hours. At the end of this time, the resulting mixture was treated and purified similarly to the procedure described in Example 1, to give 866 mg of the title compound as a powder.

Workup

  1. additionwere added to the resulting solution, whilst ice-
  2. temperaturecooling
  3. additionwas added to the resulting mixture
  4. temperatureThe mixture was then heated at 70° to 75° C. for 2.5 hours
  5. additionAt the end of this time, the resulting mixture was treated
  6. custompurified similarly to the procedure

Sources & evidence

ORD record
ord-00d49b3b9b81425a964f7c543b421b03
Source dataset
uspto-grants-1990_01
Patent number
US04894385

Reaction notes

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