CarbaMiMidothioic acid, 3-cyanopropyl ester, hydrochloride (1:1) synthesis

Yield: 62.7%

Reaction Conditions:

in waterReflux;

Steps:

1
The γ-Chlorobutyronitnle (5 0 g, 48 3 mmol) and thiourea (4 04 g, 53 1 mmol) were mixed in 40 ml of water The mixture was heated to reflux for 3 to 4 hours The reaction mixture was evaporated and 20 ml of ethanol was added and then evaporated as well This was repeated three times After that, 10 ml of methanol and 30 ml of acetone were added and the mixture was stirred for one hour The crystalline material was filtered and the product was dried under high vacuum overnight to yield 544 g (30 3 mmol, yield 62 7%) of product as white crystals, melting point 134-135°C, with purity greater than 97% ¹H NMR (300 MHz, d₆DMSO) § 1 89 (m, 2 H), 2 63 (t, 2H, J = 7 2 Hz), 3 23 (t, 2H, J = 7 2 Hz) 3 38 (s, 3H) ¹³C NMR (75 MHz) δ 15 3, 25 0, 28 8 119 8, 169 7Formula C₅H₁₀CIN₃SExact Mass 179 03MoI Wt 179 67 m/e 17903 (1000%), 18103 (321%), 18003 (74%), 18102 (45%), 18203 (20%), 18302 (15%) C 3342, H, 561,Cl, 1973, N, 2339, S, 1785 Anal Calcd 334256123391785 Found. 33.44 5.48 23.40 18.31

References:

CELLCEUTIX CORPORATION;MENON, Krishna WO2010/135170, 2010, A2 Location in patent:Page/Page column 20-21