p-Aminobenzamidine → HCID 178507442, compound

HRID 2286610Notes

Reaction equation

HRID 2286610 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 (0.642 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 minutes 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° C. for 4 hrs. After treating with a small amount of charcoal, the filtrate is added to 325 ml of 2 N HCl 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° C. dec. The product is recrystallized from dimethylacetamide-water to give 44.5 g mp 313°-314° C. dec.

Workup

  1. stirringAfter stirring for 30 min
  2. temperaturethe mixture is refluxed for 4 hrs
  3. waitto stand overnight at room temperature
  4. filtrationThe salt is filtered
  5. washwashed with isopropanol
  6. stirringstirred at 70° C. for 4 hrs
  7. additionAfter treating with a small amount of charcoal
  8. additionthe filtrate is added to 325 ml of 2 N HCl
  9. stirringwith stirring
  10. filtrationThe acid is filtered
  11. washwashed with water, ethanol, and ether
  12. customdried

Sources & evidence

ORD record
ord-f618100f4dc1401ea20ba8e237750251
Source dataset
uspto-grants-1981_05
Patent number
US04267180

Reaction notes

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