Dimethylformamide → HCID 53674222, compound

HRID 743012Notes

Reaction equation

HRID 743012 reaction equation
[K].[C:2]([O:5][C:6]1[CH:15]=[CH:14][C:13]([CH:16]=[CH:17][C:18]2[CH:23]=[CH:22][C:21]([S:24]([OH:27])(=O)=[O:25])=[CH:20][CH:19]=2)=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9])(=[O:4])[CH3:3].CN(C)C=O.S(Cl)([Cl:35])=O.[OH-].[Na+]>ClCCl.O>[C:2]([O:5][C:6]1[CH:15]=[CH:14][C:13]([CH:16]=[CH:17][C:18]2[CH:23]=[CH:22][C:21]([S:24]([Cl:35])(=[O:27])=[O:25])=[CH:20][CH:19]=2)=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9])(=[O:4])[CH3:3]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 86747764HCID 86747764, compound

Product 1

HCID 53674222HCID 53674222, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Methyl 2- acetyloxy-5-[2-(4-sulfophenyl)ethenyl]benzoate potassium salt (42.4 g, 0.104 mol) was suspended in dichloromethane. Dimethylformamide (5 ml) and thionyl chloride were added, and the mixture refluxed with stirring for 3 h. After cooling to room temperature, water (15 ml) was added. By careful addition of 5M sodium hydroxide, the pH of the aqueous phase was adjusted to about 7. The phases were separated and the organic phase washed with water. The solution was dried (MgSO4), treated with activated carbon and filtered. After evaporation of the solvent, the solid residue was recrystallized from a toluene and petroleum ethermixture. Yield 29.3 g (71%).

Workup

  1. temperaturethe mixture refluxed
  2. customThe phases were separated
  3. washthe organic phase washed with water
  4. dry with materialThe solution was dried (MgSO4)
  5. additiontreated with activated carbon
  6. filtrationfiltered
  7. customAfter evaporation of the solvent
  8. customthe solid residue was recrystallized from a toluene and petroleum ethermixture

Sources & evidence

ORD record
ord-ca0db8af28854d1590650f7491ab30d2
Source dataset
uspto-grants-1996_09
Patent number
US05556855

Reaction notes

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