Benzoic acid, 4-(aminoiminomethyl)-, ethyl ester, hydrochloride (1:1) → 4-Carbamimidoylbenzoic acid

HRID 352782Notes

Reaction equation

HRID 352782 reaction equation
Cl.[C:2]([C:5]1[CH:15]=[CH:14][C:8]([C:9]([O:11]CC)=[O:10])=[CH:7][CH:6]=1)(=[NH:4])[NH2:3]>Cl>[C:2]([C:5]1[CH:15]=[CH:14][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)(=[NH:3])[NH2:4]

Participants

3

Reactant 1

HCID 12710118Benzoic acid, 4-(aminoiminomethyl)-, ethyl ester, hydrochloride (1:1)

Product 1

HCID 35326234-Carbamimidoylbenzoic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

In 1N hydrochloric acid (100 ml), the resulting ethyl 4-amidinobenzoate hydrochloride (3.00 g) was dissolved at room temperature, followed by heating under reflux for 2 hours. The solvent was then distilled off under reduced pressure. Colorless crystalline powder so precipitated was collected by filtration and washed with a small amount of tetrahydrofuran, whereby the title compound (2.69 g, 94%) was obtained.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 2 hours
  3. distillationThe solvent was then distilled off under reduced pressure
  4. customColorless crystalline powder so precipitated
  5. filtrationwas collected by filtration
  6. washwashed with a small amount of tetrahydrofuran, whereby the title compound (2.69 g, 94%)
  7. customwas obtained

Sources & evidence

ORD record
ord-29214ab1694b432ba33f1b719eb38915
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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