Dimethylamine → Methyl 3-(dimethylcarbamoyl)benzoate

HRID 1361797Notes

Reaction equation

HRID 1361797 reaction equation
[C:1]([O:12][CH3:13])(=[O:11])[C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([O-])=[O:6])[CH:3]=1.[CH3:14][NH:15][CH3:16].CCN=C=NCCCN(C)C.Cl.O.ON1C2C=CC=CC=2N=N1>C1COCC1.CO.O>[CH3:14][N:15]([CH3:16])[C:5]([C:4]1[CH:3]=[C:2]([CH:10]=[CH:9][CH:8]=1)[C:1]([O:12][CH3:13])=[O:11])=[O:6]

Participants

8

Reactant 4

HCID 674DimethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 69512791,3-Benzenedicarboxylic acid, monomethyl ester

Product 1

HCID 12810605Methyl 3-(dimethylcarbamoyl)benzoateYield 100%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl isophthalate (2.00 g, 11.1 mmol) was dissolved in THF (60 mL), and a 2.0 mol/L solution of dimethylamine (11.1 ml, 22.2 mmol) in methanol, EDC hydrochloride (4.27 g, 22.2 mmol) and 1-hydroxybenzotriazole monohydrate (3.40 g, 22.2 mmol) were added thereto, followed by stirring at room temperature for 2 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=1:3) to afford methyl 3-(N,N-dimethylcarbamoyl)benzoate (2.30 g, 100%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled away under reduced pressure
  5. customThe resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=1:3)

Sources & evidence

ORD record
ord-0c31553c06f74a278884539d175e0632
Source dataset
uspto-grants-2011_02
Patent number
US07880013B2

Reaction notes

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