Sodium hydride → Methyl 4-[3-(4-chlorophenyl)-1-(imidazol-1-ylmethyl)propylthio]benzoate

HRID 330023Notes

Reaction equation

HRID 330023 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:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH:23](Cl)[CH2:24][N:25]2[CH:29]=[CH:28][N:27]=[CH:26]2)=[CH:17][CH:16]=1>CN(C)C=O>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH:23]([CH2:24][N:25]2[CH:29]=[CH:28][N:27]=[CH:26]2)[S:3][C:4]2[CH:5]=[CH:6][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:12][CH:13]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 237573Methyl 4-sulfanylbenzoateHCID 124320341-[2-Chloro-4-(4-chlorophenyl)butyl]-1H-imidazole

Product 1

HCID 19870506Methyl 4-[3-(4-chlorophenyl)-1-(imidazol-1-ylmethyl)propylthio]benzoateYield 43.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

11 mg of a 55% w/w suspension of sodium hydride in mineral oil were added, whilst ice-cooling, to a solution of 40 mg of methyl 4-mercaptobenzoate in 0.25 ml of dry dimethylformamide, and the resulting mixture was stirred at room temperature for 30 minutes. A solution of 52 mg of 1-[4-(4-chlorophenyl)-2-chlorobutyl]imidazole in 0.25 ml of dry dimethylformamide was added to this solution, and the resulting mixture was heated at 60°-70° C. for 5 hours. At the end of this time, the reaction mixture was treated and purified according to the same method as described in Example 1, to give 34 mg of the title compound as an oil.

Workup

  1. additionwere added, whilst ice-
  2. temperaturethe resulting mixture was heated at 60°-70° C. for 5 hours
  3. additionAt the end of this time, the reaction mixture was treated
  4. custompurified

Sources & evidence

ORD record
ord-3df47cb2946c4f6b9861e4a40f755ce2
Source dataset
uspto-grants-1990_01
Patent number
US04894385

Reaction notes

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