Hydrochloric Acid → 2-Guanidino-4-(6-aminohexyl)thiazole dihydrochloride

HRID 261437Notes

Reaction equation

HRID 261437 reaction equation
[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]2C(=O)C3=CC=CC=C3C2=O)[N:9]=1)[C:2]([NH2:4])=[NH:3].[OH-].[Na+].[ClH:29]>CO>[ClH:29].[ClH:29].[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][NH2:16])[N:9]=1)[C:2]([NH2:4])=[NH:3]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 14798Sodium Hydroxide2×HCID 178512630HCID 178512630, compound

Product 1

HCID 1784787972-Guanidino-4-(6-aminohexyl)thiazole dihydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 2-guanidino-4-(6-phthalimidohexyl)thiazole (4.2 g.) in methanol (30 ml.) and 10% w/v aqueous NaOH (10 ml.) was heated under reflux for 15 minutes. The pH of the mixture was then adjusted to 1 with concentrated HCl and the mixture heated under reflux for 30 minutes. The pH of the mixture was then adjusted to 12 with 10% w/v aqueous NaOH and the mixture heated under reflux for 15 minutes. The pH of the mixture was then adjusted to pH 1 with concentrated HCl and the mixture was heated under reflux for 30 minutes and then stirred at room temperature for 16 hours. The mixture was then evaporated to dryness in vacuo and the residue suspended in water and filtered to remove solids which were further washed with water. The combined aqueous filtrates were extracted several times with ethyl acetate, then with ether. The aqueous layer was evaporated to dryness and the residue extracted several times with ethanol. The combined ethanol extracts were evaporated to dryness, reextracted with ethanol and this extract filtered and evaporated to dryness to give 2-guanidino-4-(6-aminohexyl)thiazole dihydrochloride as a yellow foam which was used without further purification.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 15 minutes
  3. temperaturethe mixture heated
  4. temperatureunder reflux for 30 minutes
  5. temperaturethe mixture heated
  6. temperatureunder reflux for 15 minutes
  7. temperaturethe mixture was heated
  8. temperatureunder reflux for 30 minutes
  9. customThe mixture was then evaporated to dryness in vacuo
  10. filtrationfiltered
  11. customto remove solids which
  12. washwere further washed with water
  13. extractionThe combined aqueous filtrates were extracted several times with ethyl acetate
  14. customThe aqueous layer was evaporated to dryness
  15. extractionthe residue extracted several times with ethanol
  16. customThe combined ethanol extracts were evaporated to dryness
  17. filtrationthis extract filtered
  18. customevaporated to dryness

Sources & evidence

ORD record
ord-61ac53b48b664e57bed71e0d4b66b84e
Source dataset
uspto-grants-1979_08
Patent number
US04165377

Reaction notes

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