Hydrochloric Acid → 2-Guanidino-4-(4-aminobutyl)thiazole hydrobromide hydrochloride

Temperature

100 °C

A mixture of 2-guanidino-4-(4-phthalimidobutyl)thiazole hydrobromide (3.43 g.) and potassium hydroxide (1.68 g.) in water (50 ml.) was heated at 100° C. for 15 minutes. The reaction mixture was then acidified to pH 2 with 2 N HCl, and the mixture heated at 100° C. for 1 hour. The cooled reaction mixture was extracted three times with ethyl acetate, the aqueous layer was evaporated to dryness and to the residue was added toluene which was evaporated to dryness. The resulting gummy solid was dissolved in methanol, the insoluble material filtered off and the filtrate evaporated to dryness to give 2-guanidino-4-(4-aminobutyl)thiazole hydrobromide hydrochloride. The free base (1.2 g.) was obtained by passage down an ion-exchange column [Amberlite IRA-400 (OH)] in 50% v/v methanol/water.

1. temperaturethe mixture heated at 100° C. for 1 hour
2. customThe cooled reaction mixture
3. extractionwas extracted three times with ethyl acetate
4. customthe aqueous layer was evaporated to dryness and to the residue
5. additionwas added toluene which
6. customwas evaporated to dryness
7. dissolutionThe resulting gummy solid was dissolved in methanol
8. filtrationthe insoluble material filtered off
9. customthe filtrate evaporated to dryness

ORD record

ord-880659e2ddc54d6d9af3b5895b3f525b

Source dataset

uspto-grants-1979_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04165377