Hydrochloric Acid → Methyl 3-[({2-[(diaminomethylidene)amino]-1,3-thiazol-4-yl}methyl)sulfanyl]propanimidate

Temperature

2 °C

3-(2-Guanidino-4-thiazolylmethylthio)propionitrile (12.82 g) was dissolved in a mixture of dry methanol (75 ml) and dry chloroform (150 ml) and the stirred solution was cooled (under nitrogen) in an ice-salt bath to 2° C. Hydrogen chloride gas (dried) was passed through the solution for three hours, keeping the temperature at 0°-10° C. The solution was then allowed to stand in a stoppered flask at ca 0° C. for 20 hours. The solvents were removed at reduced pressure and the oily residue added to ice-water (200 ml) containing potassium carbonate (30 g). The mixture was extracted with chloroform containing 20% methanol (4×150 ml) and the combined organic extracts were dried (MgSO4). The solvent was removed to give methyl 3-(2-guanidino-4thiazolylmethylthio)propionimidate (13.60 g) as a tacky light-brown oil.

1. customat 0°-10° C
2. customThe solvents were removed at reduced pressure
3. additionthe oily residue added to ice-water (200 ml)
4. additioncontaining potassium carbonate (30 g)
5. extractionThe mixture was extracted with chloroform containing 20% methanol (4×150 ml)
6. dry with materialthe combined organic extracts were dried (MgSO4)
7. customThe solvent was removed

ORD record

ord-72dc51d1970b411f9018a0d8a1689d0f

Source dataset

uspto-grants-1989_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04808589