Hydrochloric Acid → Bis-guanidine dihydrochloride

The N′,N″-di-BOCguanidine (0.45 g, 0.60 mmol) was dissolvedin CH2Cl2 (10 mL), diluted with dry EtOH (15 mL) and the chilled solution was saturated with dry HCl. The reaction was then kept stirring at room temperature for 3 days (drying tube), when by the product started forming a precipitate over time. After evaporating the solvent to dryness, the residue was washed with ether multiple times and was dried under vacuum at 50-60° C. over night to give whitish yellow solid of the bis-guanidine dihydrochloride; mp>300° C. 1H NMR (DMSO-d6): δ 7.85 (dd, J=1.5, 8.4 Hz, 4H), 7.92 (d, J=1.2 Hz, 4H), 8.00 (dd, J=1.5, 8.4 Hz, 4H ), 9.09 (br s, 4H), 11.25 (br s, 2H). 13C NMR (DMSO-d6): δ 155.98, 138.35, 137.32, 135.00, 127.79, 127.22, 124.79. MS (ESI) m/e (rel. int.): 344 (M+, 6), 173 (100). Anal. Calc. for C20H20N6-2.0HCl-1.0H2O-0.2C2H5OH: C %, 55.11; H %, 5.71; N %, 18.90. Found C %, 55.39; H %, 5.50; N %, 18.71.

1. custom(drying tube), when by the product
2. customstarted forming a precipitate over time
3. customAfter evaporating the solvent to dryness
4. washthe residue was washed with ether multiple times
5. customwas dried under vacuum at 50-60° C. over night

ORD record

ord-58621fac3ff84331a967aac9e86f46fb

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08101636B2