p-Aminobenzamidine → HCID 178507442, compound

HRID 1447154Notes

Reaction equation

HRID 1447154 reaction equation
[Na].[NH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[NH:8])=[CH:5][CH:4]=1.C([O:14][CH:15]=[C:16]([C:22](OCC)=O)[C:17]([O:19]CC)=[O:18])C>C(O)C>[NH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]2[N:9]=[C:15]([OH:14])[C:16]([C:17]([OH:19])=[O:18])=[CH:22][N:8]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 1725p-AminobenzamidineHCID 6871Diethyl (ethoxymethylene)malonateHCID 5360545Sodium

Product 1

HCID 178507442HCID 178507442, compoundYield 102,671.102%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 14.8 g (0.641 mmol) of sodium in 750 ml of dry ethanol is stirred at 0° and 44.6 g (0.214 mmol) of 4-aminobenzamidine.2HCl [Shaw and Cooley, J. Am. Chem. Soc., 79, 3561 (1957)] is added. The mixture is stirred 5 min under nitrogen and 46.2 g (0.214 mmol) of diethyl ethoxymethylenemalonate is added. After stirring for 30 min, the mixture is refluxed for 4 hrs and allowed to stand overnight at room temperature. The salt is filtered and washed with isopropanol. The salt is suspended in 214 ml of 2 N potassium hydroxide and stirred at 70° for 4 hr. After treating with a small amount of charcoal, the filtrate is added to 325 ml of 2 N hydrochloric acid with stirring. The acid is filtered, washed with water, ethanol, and ether, and dried to give 50.8 g of the title compound, mp 312°-314° dec. The product is recrystallized from N,-N-dimethylacetamide-water to give 44.5 g mp 313°-314° dec.

Workup

  1. addition2HCl [Shaw and Cooley, J. Am. Chem. Soc., 79, 3561 (1957)] is added
  2. stirringAfter stirring for 30 min
  3. temperaturethe mixture is refluxed for 4 hrs
  4. waitto stand overnight at room temperature
  5. filtrationThe salt is filtered
  6. washwashed with isopropanol
  7. stirringstirred at 70° for 4 hr
  8. additionAfter treating with a small amount of charcoal
  9. additionthe filtrate is added to 325 ml of 2 N hydrochloric acid
  10. stirringwith stirring
  11. filtrationThe acid is filtered
  12. washwashed with water, ethanol, and ether
  13. customdried

Sources & evidence

ORD record
ord-1169a7f280d549a1affc461b18082438
Source dataset
uspto-grants-1982_02
Patent number
US04315933

Reaction notes

Loading…