Sodium hydride → HCID 19870518, compound

HRID 330013Notes

Reaction equation

HRID 330013 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[CH3:28])[CH2:16][N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1>CN(C)C=O>[CH3:28][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 19870519HCID 19870519, compound

Product 1

HCID 19870518HCID 19870518, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1.64 g of methyl 4-mercaptobenzoate was dissolved in 10.4 ml of dry dimethylformamide, and 424 mg of a 55% w/w suspension of sodium hydride in mineral oil were added, whilst ice-cooling. The resulting mixture was then stirred at room temperature for 30 minutes. 12 ml of dry dimethylformamide containing 2.15 g of 1-[2-chloro-2-(2-methylphenyl)ethyl]imidazole were added to the resulting solution, and the mixture was heated at a temperature between 60° and 70° C. for 5.5 hours. At the end of this time, the resulting solution was treated and purified by the same procedure as described in Example 1, to give 2.62 g of the title compound as an oil.

Workup

  1. additionwere added, whilst ice-
  2. temperaturecooling
  3. temperaturethe mixture was heated at a temperature between 60° and 70° C. for 5.5 hours
  4. additionAt the end of this time, the resulting solution was treated
  5. custompurified by the same procedure

Sources & evidence

ORD record
ord-75e8a50f6d9045898e06afe8fc4c2012
Source dataset
uspto-grants-1990_01
Patent number
US04894385

Reaction notes

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