Water → HCID 53748468, compound

HRID 1719663Notes

Reaction equation

HRID 1719663 reaction equation
[C:1]1([C:7]2[CH:19]=[CH:18][C:10]([C:11]([CH:13]=[CH:14][C:15]([OH:17])=[O:16])=[S:12])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(OC)(O[CH3:24])(=O)=O.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:1]1([C:7]2[CH:19]=[CH:18][C:10]([C:11]([CH:13]=[CH:14][C:15]([O:17][CH3:24])=[O:16])=[S:12])=[CH:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 53824855HCID 53824855, compound

Product 1

HCID 53748468HCID 53748468, compoundYield 75.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 8.53 g of 3-(4-phenylthiobenzoyl)acrylic acid in 50 ml of dimethylformamide were added 4.54 g of dimethyl sulfate and 2.50 g of potassium carbonate, and the resulting mixture was stirred at room temperature for 3 hours. To the reaction solution was added water, and the mixture was extracted from diethyl ether. The organic layer was washed, in turn, with water, a saturated aqueous solution of sodium hydrogen-carbonate and water, and dried over magnesim sulfate. The diethyl ether was removed from the solution by evaporation, and the residue was recrystallized from a mixture of hexane and dichloromethane to give 6.80 g of methyl 3-(4-phenylthiobenzoyl)acrylate.

Workup

  1. extractionthe mixture was extracted from diethyl ether
  2. washThe organic layer was washed, in turn, with water
  3. dry with materiala saturated aqueous solution of sodium hydrogen-carbonate and water, and dried over magnesim sulfate
  4. customThe diethyl ether was removed from the solution by evaporation
  5. customthe residue was recrystallized from a mixture of hexane and dichloromethane

Sources & evidence

ORD record
ord-c87af4ad62ae415f8b68703c4ae48285
Source dataset
uspto-grants-1985_09
Patent number
US04541959

Reaction notes

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