Dimethylamine → 4-(Dimethylcarbamoyl)benzoic acid

HRID 2416574Notes

Reaction equation

HRID 2416574 reaction equation
[Cl-].[C:2]([O:13]C)(=O)[C:3]1[CH:11]=[CH:10][C:6]([C:7]([O-:9])=[O:8])=[CH:5][CH:4]=1.[OH-].[Na+].[CH3:17][NH:18][CH3:19]>O1CCOCC1>[CH3:17][N:18]([CH3:19])[C:2]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)=[O:13]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 14798Sodium HydroxideHCID 22493623Monomethyl terephthalate chloride

Product 1

HCID 110954804-(Dimethylcarbamoyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 5 g (25.2 mmol) of monomethyl terephthalate chloride in 20 ml of dioxane was dissolved in 30 ml of 50% aqueous dimethylamine solution under cooling with ice. After stirring for 30 minutes, 50 ml of 1 N aqueous sodium hydroxide solution was added to the reaction mixture, and they were stirred at room temperature for 2 days. The reaction liquid was washed with ethyl acetate and acidified with hydrochloric acid. After the extraction with ethyl acetate, the extract was washed with saturated aqueous salt solution and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was washed with hexane and dried to obtain the title compound.

Workup

  1. temperatureunder cooling with ice
  2. stirringwere stirred at room temperature for 2 days
  3. customThe reaction liquid
  4. washwas washed with ethyl acetate
  5. extractionAfter the extraction with ethyl acetate
  6. washthe extract was washed with saturated aqueous salt solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated
  9. washthe residue was washed with hexane
  10. customdried

Sources & evidence

ORD record
ord-1a29f97085454220827ebaa06b58bf05
Source dataset
uspto-grants-2004_11
Patent number
US06825181B1

Reaction notes

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