Sodium Chloride → HCID 15055900, compound

HRID 330003Notes

Reaction equation

HRID 330003 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][CH:23]=1)[CH2:16][N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1.[Cl-].[Na+]>CN(C)C=O>[C:22]1([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][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 237573Methyl 4-sulfanylbenzoateHCID 14098071HCID 14098071, compound

Product 1

HCID 15055900HCID 15055900, compoundYield 30.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1.5 g of methyl 4-mercaptobenzoate was dissolved in 8 ml of dry dimethylformamide, and the resulting solution was added to 388 mg of a 55% w/w suspension of sodium hydride in mineral oil, whilst ice-cooling, and then the mixture was stirred at room temperature for 30 minutes. A solution of 1.5 g of 1-(2-chloro-2-phenylethyl)imidazole dissolved in 8 ml of dry dimethylformamide was added to the thus obtained solution, and the mixture was then heated at 65° to 70° C. for 6 hours. At the end of this time, the reaction mixture was poured into a saturated aqueous solution of sodium chloride, and the resulting solution was extracted with diethyl ether. The extract was washed with water and dried over anhydrous potassium carbonate, and then the solvent was removed by distillation. The residue was purified by column chromatography through silica gel (eluent: ethyl acetate:triethylamine=40:1 by volume) to obtain 747 mg of the title compound as a colorless powder.

Workup

  1. temperaturecooling
  2. additionwas added to the thus obtained solution
  3. temperaturethe mixture was then heated at 65° to 70° C. for 6 hours
  4. extractionthe resulting solution was extracted with diethyl ether
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous potassium carbonate
  7. customthe solvent was removed by distillation
  8. customThe residue was purified by column chromatography through silica gel (eluent: ethyl acetate:triethylamine=40:1 by volume)

Sources & evidence

ORD record
ord-98e042f4fdfa4f6687a809095861ea77
Source dataset
uspto-grants-1990_01
Patent number
US04894385

Reaction notes

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