N,N'-DICYCLOHEXYLDITHIOOXAMIDE synthesis
- Product Name:N,N'-DICYCLOHEXYLDITHIOOXAMIDE
- CAS Number:122-36-1
- Molecular formula:C14H24N2S2
- Molecular Weight:284.48
Yield:122-36-1 76.7%
Reaction Conditions:
with sulfur in 2-methoxy-ethanol;N,N-dimethyl-formamide at 100; for 16 h;Willgerodt-Kindler Rearrangement;Solvent;Temperature;Time;
Steps:
1,2-Bis(cyclohexylamino)ethane-1,2-dithione (1).
a. A mixture of 1742 mg (10.51 mmol) of tetrachloroethylene, 1011 mg (31.53 mmol) of finely ground sulfur, 5213 mg (52.56 mmol) of cyclohexylamine, 5.5 mL of DMF (DMF-C2Cl4 3 : 1 w/w), and 4 mL of methyl cellosolve was stirred at 100°C for 16 h. After completion of the reaction, the reaction mixture was poured into a beaker with 30-40 mL of distilled water and, after through mixing, neutralized with 2-3% HCl. The resulting product was fi ltered off, washed on the fi lter with distilled water, and left there to dry completely to obtain 1670 mg (89.4%) of a crude compound 1, mp 143-144°C. The crude product was recrystallized from propan-2-ol to give 1433 mg (76.7%) of a pure compound 1, mp 150-151°C (151-152°C [15], 149.0-149.5°C [11]). 1H NMR spectrum (CDCl3), δ, ppm: 1.35 m (2H, CH2), 1.47 m (8H, 4CH2), 1.68 m (2H, CH2), 1.79 m (4H, 2CH2), 2.07 m (4H, 2CH2), 4.26 m (2H, 2CH), 10.37 s (2H, 2NH). 13C NMR spectrum (CDCl3), δ, ppm: 24.31 (CH2), 25.42 (CH2), 30.60 (CH2), 55.77 (CHN), 182.97 (C=S). ESI-HRMS: m/z 283.1310 [M - H]-. C14H23N2S2. Calculated: 283.1308 [M - H]-; m/z 307.1272 [M + Na]+. C14H24N2NaS2. Calculated 307.1274 [M + Na]+.
References:
Boyarskii, V. P.;Eliseenkov, E. V.;Petrov, A. A.;Ponomareva, T. N. [Russian Journal of Organic Chemistry,2020,vol. 56,# 5,p. 781 - 787][Zh. Org. Khim.,2020,vol. 56,# 5,p. 726 - 734,9]
