Hydrochloric Acid → HCID 178512815, compound

HRID 1462995Notes

Reaction equation

HRID 1462995 reaction equation
[ClH:1].[NH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]([NH2:15])=[NH:14])[C:3]([NH2:5])=[NH:4].NCCCCCCN.Cl>>[Cl-:1].[NH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]([NH2:15])=[NH:14])[C:3]([NH2:5])=[NH:4]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 16402HexamethylenediamineHCID 178479435HCID 178479435, compound

Product 1

HCID 178512815HCID 178512815, compound

Conditions

Temperature
80 °C

Procedure

The diguanidinium salts may be prepared by the conventional method of reacting a diamine salt (XH.H2N--R--NH2.HX) with cyanamid (H2N--C≡N, R and X being as hereinabove mentioned). An amine salt or a mixture of amine salts may also be used. The molar ratio between the diamine salt and the cyanamid is at least 1:2. By way of example, 1,6-bisguanidinohexane hydrochloride, having the formula: ##STR2## is prepared from 1,6-diaminohexane and cyanamid by introducing 1 mole of diamine, which has been previously dried and dissolved in isopropyl alcohol, into a flask equipt with a stirrer, a thermometer and an outlet tube linked to a Dan and Stark decanter provided with a water cooler. Then, 3 moles of hydrochloric acid are slowly introduced into the flask. After reaction, the water and isopropyl alcohol are removed. Xylene is then added and the mixture is heated under reflux in order to remove any remaining traces of water. When the mixture has cooled down to about 80° C., 2 moles of cyanamid are added to it and the reaction mixture is heated to 140° C. and held there for 2 hours. After cooling, the reaction mixture is filtered, washed with alcohol, stirred at 60° C. for 30 minutes in the presence of alcohol containing about 1% active carbon, and filtered on a millipore filter. After elimination of residual solvent, 1,6-bisguanidinohexane chloride is obtained with a purity of about 98%.

Workup

  1. customhas been previously dried
  2. dissolutiondissolved in isopropyl alcohol, into a flask equipt with a stirrer
  3. customprovided with a water cooler
  4. customAfter reaction
  5. customthe water and isopropyl alcohol are removed
  6. additionXylene is then added
  7. temperaturethe mixture is heated
  8. temperatureunder reflux in order
  9. customto remove any remaining traces of water
  10. addition2 moles of cyanamid are added to it
  11. temperaturethe reaction mixture is heated to 140° C.
  12. temperatureAfter cooling
  13. filtrationthe reaction mixture is filtered
  14. washwashed with alcohol
  15. filtrationfiltered on a millipore
  16. filtrationfilter

Sources & evidence

ORD record
ord-b1ece71764464954bd5cd5028cc04df5
Source dataset
uspto-grants-1984_07
Patent number
US04462910

Reaction notes

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