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

HRID 224981Notes

Reaction equation

HRID 224981 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-ec3f5d95741a4b0c8d33484639cf1c00
Source dataset
uspto-grants-1980_11
Patent number
US04234735

Reaction notes

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