Dimethylamine → ethyl 4-(N,N-dimethylamidino)benzoate

HRID 747670Notes

Reaction equation

HRID 747670 reaction equation
Cl.C(O[C:5]([C:7]1[CH:17]=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=1)=[NH:6])C.[CH3:18][NH:19][CH3:20]>C(O)C>[CH3:18][N:19]([CH3:20])[C:5]([C:7]1[CH:17]=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=1)=[NH:6]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 68830640Ethyl 4-ethoxycarbonimidoylbenzoate hydrochloride

Product 1

HCID 22631319ethyl 4-(N,N-dimethylamidino)benzoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1 g (3.9 mmol) of ethyl 4-ethoxycarbonimidoylbenzoate hydrochloride was stirred in a mixture of 3 ml of ethanol and 10 ml of 50% aqueous dimethylamine solution overnight. Then the solvent was evaporated, and 10 ml of dioxane containing 4 N hydrogen chloride and 1 ml of ethanol were added to the residue. After stirring at room temperature for 5 days, the solvent was evaporated. 1 N sodium hydroxide was added to the residue. After the extraction with dichloromethane, the organic layer was washed with saturated Aqueous NaCl solution and dried over anhydrous magnesium sulfate. The solvent was evaporated to obtain the title compound.

Workup

  1. customThen the solvent was evaporated
  2. addition10 ml of dioxane containing 4 N hydrogen chloride and 1 ml of ethanol were added to the residue
  3. customthe solvent was evaporated
  4. addition1 N sodium hydroxide was added to the residue
  5. extractionAfter the extraction with dichloromethane
  6. washthe organic layer was washed with saturated Aqueous NaCl solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated

Sources & evidence

ORD record
ord-0cc42a4a09e1470db033722a0a9aeb69
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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