Chloroformamidine hydrochloride

white powder

Synthesis of chloroformamidine hydrochloride; A solution of cyanamide (50.0 g, 1.19 mol, 1 eq) in diethylether (900 ml) is cooled to 0 °C and then hydrogen chloride in diethyl ether (450 g, 29percent) is added maintaining the temperature below +5 °C. After the addition is complete, the obtained white suspension is stirred further at room temperature for a short time, the white precipitate is filtered off and dried in vacuo at 30 °C. A white solid (132.66 g, 1.15 mol, 96.64percent) is obtained.Cyanamide (4.2 g, 0.1 mol) was dissolved in 100 mL of diethyl ether in a 500 mL round bottom flask. The mixture was stirred under nitrogen. 100 mL of 2M HCl in diethyl ether was added to the reaction flask via a 250 mL dropping funnel. Stirring was continued for 2 hours at room temperature. The white salt which precipitated out was filtered and dried. The overall yield for 7 was 96percent. 7 was used for the next step without further purification.Chloroformamidine hydrochloride Experimental procedure taken from Henderson et al. [22]. Cyanamide (1.00 g, 23.8 mmol) was dissolved in acetic anhydride (75.0 ml_) and hydrogen chloride gas was passed through the ice-cooled solution via a wide glass tube for 2.5 h forming a white precipitate. The product was collected by filtration, washed well with acetic anhydride and petroleum ether and dried in vacuo to yield a white solid (2.62 g, 95.9 percent). Mp = 175-177 °C. 100 mL (12 M) HCl was poured in a 250 mL flask and cooled to 0°C. Cyanamide (10 g, 233 mmol) was added in portions and stirred for 2 hours at room temperature. The resulting mixture was then concentrated to about 40 mL and a white precipitate was formed. After cooling down to 0°C with an ice-bath, the precipitate was filtered off and the crystals were washed with HCl (6 M) to yield 6.80 g (52.9 mmol, 25.4percent) as a crystalline white solid. The compound was characterized by its melting point. Mp 176-180

Molecular Weight:114.96
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:1
Exact Mass:113.9751535
Monoisotopic Mass:113.9751535
Topological Polar Surface Area:49.9
Heavy Atom Count:5
Complexity:33
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes