N-(4,5-Dihydro-2-thiazolyl)cyanamide

Into a solution of 26.5 g of sodium carbonate in 150 ml of water are metered, at room temperature, 28.8 g of cysteamine hydrochloride. The reaction mixture is cooled to 10Example 3Into a solution of 23.8 g of sodium hydrogencarbonate in 200 ml of water are metered, at room temperature, 28.8 g of cysteamine hydrochloride. The reaction mixture is cooled to 10Add 300 ml of water to the three-necked bottle, then add 16.4 g of sodium hydroxide, stir and dissolve, Cool down to below 10 °C, Rapid addition of cysteamine hydrochloride 56g (0.50 mol), After stirring and dissolving, The temperature was lowered to 0 to 5 ° C, and then a compound HRB-1365-0 (cyanimide dimethyl ester molecular formula: C4H6N2S2) 61 g (0.41 mol) was added, and after stirring for 40 minutes, the reaction was completed and filtered.The filter cake was washed with 200 ml of water, the filter cake was white solid, and the wet product was 57 g.Drying under reduced pressure at 60-65 ° C gave a white crystalline solid 46 g.That is, the compound HRB-1365-2 (2-cyanoimido-1, 3-thiazolidine molecular formula: C4H5N3S), The yield was 87.5percent, and the HPLC (High Performance Liquid Chromatograph) content was ≥99percent.A 1 litre four-necked flask provided with a thermometer and stirrer is charged with 9Og of methanol (2.815 moles) and 36g of sodium methoxide (0.667 moles, 1.3 mole equivalent based upon 1.1 mole equivalent of 2-aminoethane thiol hydrochloride) under nitrogen. The mixture is cooled and stirred to dissolve in Comparative Comparative At first, water (5.Og) and aqueous phase from the methylation (5.Og, which containing approximately 0.0046 moles of the sodium methyl N-cyanodithioiminocarbonate, prepared as in Example 4 above) were taken in a 250 ml round bottom flask. The remaining aqueous phase from the methylation (71 .4g, containing approximately 0.066 moles of the sodium methyl N-cyanodithioiminocarbonate) and 70percent aqueous solution of 2- chloroethylammonium hydrochloride (20.0g, 70percent aqueous solution, 0.12 moles) were mixed in an addition funnel and this mixture was added to the flask over 4 hours at 70 —75°C maintaining the pH of the reaction mixture between 6.3 and 6.8 with concomitant addition of 50percent aqueous NaOH. The rest of the procedure was the same as in Example 4 above. Here, the weight of the dried CIT product was 6.9g with a purity of 97.8percent. The organic impurities as seen on LC were 0.9percent while the rest were inorganic salts, for example, sodium methyl sulfate and sodium chloride. The isolated yield of CIT based on cyanamide was 5 6.9percent.Reference Example 1Into a solution of 26.5 g of sodium carbonate in 150 ml of water are metered, at room temperature, 28.8 g of cysteamine hydrochloride. The reaction mixture is cooled to 10Example 3Into a solution of 23.8 g of sodium hydrogencarbonate in 200 ml of water are metered, at room temperature, 28.8 g of cysteamine hydrochloride. The reaction mixture is cooled to 10Add 300 ml of water to the three-necked bottle, then add 16.4 g of sodium hydroxide, stir and dissolve, Cool down to below 10 °C, Rapid addition of cysteamine hydrochloride 56g (0.50 mol), After stirring and dissolving, The temperature was lowered to 0 to 5 ° C, and then a compound HRB-1365-0 (cyanimide dimethyl ester molecular formula: C4H6N2S2) 61 g (0.41 mol) was added, and after stirring for 40 minutes, the reaction was completed and filtered.The filter cake was washed with 200 ml of water, the filter cake was white solid, and the wet product was 57 g.Drying under reduced pressure at 60-65 ° C gave a white crystalline solid 46 g.That is, the compound HRB-1365-2 (2-cyanoimido-1, 3-thiazolidine molecular formula: C4H5N3S), The yield was 87.5percent, and the HPLC (High Performance Liquid Chromatograph) content was ≥99percent.A 1 litre four-necked flask provided with a thermometer and stirrer is charged with 9Og of methanol (2.815 moles) and 36g of sodium methoxide (0.667 moles, 1.3 mole equivalent based upon 1.1 mole equivalent of 2-aminoethane thiol hydrochloride) under nitrogen. The mixture is cooled and stirred to dissolve in Comparative Comparative At first, water (5.Og) and aqueous phase from the methylation (5.Og, which containing approximately 0.0046 moles of the sodium methyl N-cyanodithioiminocarbonate, prepared as in Example 4 above) were taken in a 250 ml round bottom flask. The remaining aqueous phase from the methylation (71 .4g, containing approximately 0.066 moles of the sodium methyl N-cyanodithioiminocarbonate) and 70percent aqueous solution of 2- chloroethylammonium hydrochloride (20.0g, 70percent aqueous solution, 0.12 moles) were mixed in an addition funnel and this mixture was added to the flask over 4 hours at 70 —75°C maintaining the pH of the reaction mixture between 6.3 and 6.8 with concomitant addition of 50percent aqueous NaOH. The rest of the procedure was the same as in Example 4 above. Here, the weight of the dried CIT product was 6.9g with a purity of 97.8percent. The organic impurities as seen on LC were 0.9percent while the rest were inorganic salts, for example, sodium methyl sulfate and sodium chloride. The isolated yield of CIT based on cyanamide was 5 6.9percent.Reference

Molecular Weight:127.17
XLogP3:0.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:127.02041835
Monoisotopic Mass:127.02041835
Topological Polar Surface Area:73.5
Heavy Atom Count:8
Complexity:154
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes