Chloroform → 2-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazole

Following the above procedure, 10.1 millimoles of 2-(methylaminomethyl)-4-thiazolemethanol dihydrochloride, 1.15 g. of cysteamine hydrochloride and 15 ml. of 48% aqueous hydrobromic acid were stirred at about 100° C. for about 7.5 hours. Water and hydrobromic acid were removed on a rotary evaporator and the resulting residue comprising 2-(2-methylaminomethyl-4-thiazolylmethylthio)ethylamine trihydrobromide formed in the above reaction was dissolved in water and the water removed by evaporation. The residue was again taken up in water and the water removed by evaporation. The residue was then dissolved in a small volume of water and a solution of 5.5 g. of potassium carbonate in 15 ml. of water was added. The resulting alkaline solution was evaporated to dryness. The resulting residue, comprising the free base of 2-(2-methylaminomethyl-4-thiazolylmethylthio)ethylamine, was slurried with ethanol and the ethanol separated and removed by evaporation. The residue was twice slurried with isopropanol. The residue was next extracted with boiling isopropanol several times and the combined isopropanol extracts combined and filtered. Removal of the isopropanol yielded a yellow oil. The yellow oil was dissolved in chloroform and the chloroform solution filtered. Chloroform was evaporated from the filtrate to yield 1.59 g. of a yellow oil comprising 2-(2-methylaminomethyl-4-thiazolylmethylthio)ethylamine. The compound had the following physical characteristics:

1. customthe water removed by evaporation
2. customthe water removed by evaporation
3. dissolutionThe residue was then dissolved in a small volume of water
4. additionof water was added
5. customThe resulting alkaline solution was evaporated to dryness
6. customthe ethanol separated
7. customremoved by evaporation
8. extractionThe residue was next extracted with boiling isopropanol several times
9. filtrationfiltered
10. customRemoval of the isopropanol
11. customyielded a yellow oil
12. filtrationthe chloroform solution filtered
13. customChloroform was evaporated from the filtrate
14. customto yield 1.59 g

ORD record

ord-a9745e2fbe9740d3a787f212cf137982

Source dataset

uspto-grants-1990_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04904792