Dimethylamine → 4-(Dimethylcarbamoyl)benzoic acid

HRID 747704Notes

Reaction equation

HRID 747704 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11](Cl)=[O:12])=[CH:7][CH:6]=1)=[O:4].[CH3:14][NH:15][CH3:16].[OH-].[Na+]>O1CCOCC1>[CH3:14][N:15]([CH3:16])[C:11]([C:8]1[CH:9]=[CH:10][C:5]([C:3]([OH:2])=[O:4])=[CH:6][CH:7]=1)=[O:12]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 14798Sodium HydroxideHCID 81850Methyl 4-(chlorocarbonyl)benzoate

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 methyl 4-chlorocarbonyl benzoate in 20 ml of dioxane was added to 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 resultant mixture, and they were stirred at room temperature for 2 days. The reaction liquid was washed with ethyl acetate and made acidic with hydrochloric acid. After the extraction with ethyl acetate, the extract was washed with saturated Aqueous NaCl 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 NaCl 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-3b1983c1e5514ba68b23a1f1ab5fa0d1
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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