Guanidine Hydrochloride → HCID 178433869, compound

Temperature

70 °C

Guanidine hydrochloride (2.42 g, 25.32 mmol) was dissolved in 20 ml of anhydrous methanol and then treated with sodium methoxide (1.50 g, 27.83 mmol), added in one portion at room temperature. The reaction mixture was stirred under nitrogen for 1 hour, then filtered under a nitrogen atmosphere. The solids were washed with anhydrous methanol (3×10 ml) and the filtrate concentrated under reduced pressure. Anhydrous benzene (60 ml) was added to the residue, the mixture reconcentrated in vacuo and the residue was dried under high vacuum. Anhydrous dimethylformamide (10 ml), anhydrous tetrahydrofuran (20 ml) and methyl 4-methyl-2-phenyl-2H-1,2,3-triazole-5-carboxylate (1.00 g, 4.60 mmol) were added to the solid residue and the resulting mixture was heated at 70° C. under nitrogen for 7 h, then stirred at ambient temperature overnight. The reddish colored solution was then diluted with water (90 ml) to give the free base corresponding to the title compound as a tan solid (0.53 g, 47% yield).

1. additionadded in one portion at room temperature
2. filtrationfiltered under a nitrogen atmosphere
3. washThe solids were washed with anhydrous methanol (3×10 ml)
4. concentrationthe filtrate concentrated under reduced pressure
5. additionAnhydrous benzene (60 ml) was added to the residue
6. customthe residue was dried under high vacuum
7. stirringstirred at ambient temperature overnight

ORD record

ord-681c085159074b1aa0c6834835ee9377

Source dataset

uspto-grants-2005_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06974813B2