Hydrochloric Acid → HCID 20373299, compound

HRID 1834404Notes

Reaction equation

HRID 1834404 reaction equation
[ClH:1].C(C1C=CC(C2[O:14]C(C#N)=CC=2)=CC=1)#N.Cl.Cl.[NH:19]=[C:20](OC)[C:21]1[CH:26]=[CH:25][C:24]([C:27]2[O:31][C:30]([C:32](=[NH:35])OC)=[CH:29][CH:28]=2)=[CH:23][CH:22]=1.C([O-])(=O)C.[NH4+:42].[NH4+:43].[OH-]>CO>[OH2:14].[ClH:1].[ClH:1].[C:20]([C:21]1[CH:26]=[CH:25][C:24]([C:27]2[O:31][C:30]([C:32]([NH2:35])=[NH:43])=[CH:29][CH:28]=2)=[CH:23][CH:22]=1)(=[NH:42])[NH2:19]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 517165Ammonium AcetateHCID 20373301HCID 20373301, compoundHCID 20373304HCID 20373304, compound

Product 1

HCID 20373299HCID 20373299, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dry HCl was passed into a solution of 5-(4-cyanophenyl)-2-furonitrile (10 g, 0.052 mole) in absolute methanol (100 ml) with stirring at 10°-15° for 3 hours until saturated. The product was collected by filtration; yield: 12 g (71%). A mixture of methyl 5-(4-[imino(methoxy)methyl]phenyl)-2-furimidate dihydrochloride (12 g, 0.036 mole), ammonium acetate (140 g) and absolute alcohol (550 ml) was refluxed for 6 hours and stored overnight at room temperature. The mixture was poured onto ice, adjusted to pH 8 with NH4OH and the solution concentrated to one half its volume. More H2O (800 ml) was added and the product was collected by filtration. After air drying, the product was dissolved in isopropanol, adjusted to pH 3 with ethanol-HCl and ether was added until cloudiness appeared. The solution was cooled and the solid was collected by filtration to yield 9 g (83%) of 5-( 4-amidinophenyl)-2-furamidine dihydrochloride monohydrate, m.p. > 300°.

Workup

  1. filtrationThe product was collected by filtration
  2. temperaturewas refluxed for 6 hours
  3. waitstored overnight at room temperature
  4. additionThe mixture was poured onto ice
  5. concentrationthe solution concentrated to one half its volume
  6. additionMore H2O (800 ml) was added
  7. filtrationthe product was collected by filtration
  8. customAfter air drying
  9. dissolutionthe product was dissolved in isopropanol
  10. additionwas added until cloudiness
  11. temperatureThe solution was cooled
  12. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-1c907320aa1d45d0a5df0e6c621aaa12
Source dataset
uspto-grants-1978_01
Patent number
US04070380

Reaction notes

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