Sodium hydride → HCID 13913551, compound

HRID 330004Notes

Reaction equation

HRID 330004 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]([Cl:28])=[CH:24][C:23]=1[Cl:29])[CH2:16][N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1>CN(C)C=O>[Cl:29][C:23]1[CH:24]=[C:25]([Cl:28])[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 124607821-[2-Chloro-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole

Product 1

HCID 13913551HCID 13913551, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

415 mg of methyl 4-mercaptobenzoate were dissolved in 3 ml of dry dimethylformamide, and 108 mg of a 55% w/w suspension of sodium hydride in mineral oil were then added to the resulting solution, whilst ice-cooling, after which the mixture was stirred at room temperature for 30 minutes. 567 mg of a solution of 1-[2-chloro-2-(2,4-dichlorophenyl)ethyl]imidazole dissolved in 3 ml of dry dimethylformamide were then added to the resulting solution, and the mixture was heated at 60° to 70° C. for 7 hours. At the end of this time, the resulting mixture was treated and purified similarly to the procedure described in Example 1, to give 317 mg of the title compound as colorless crystals, melting at 121°-124° C.

Workup

  1. additionwere then added to the resulting solution, whilst ice-
  2. temperaturecooling
  3. additionwere then added to the resulting solution
  4. temperaturethe mixture was heated at 60° to 70° C. for 7 hours
  5. additionAt the end of this time, the resulting mixture was treated
  6. custompurified similarly to the procedure

Sources & evidence

ORD record
ord-50ca0ba7a3994603866fccc856d122b4
Source dataset
uspto-grants-1990_01
Patent number
US04894385

Reaction notes

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