Reaction of carbohydrazide with carbon disulphide; Hydrazine Carbodithio Potassium Salt
SyntheticPage 300
DOI:
10.1039/SP300
Submitted Jan 06, 2010, published Sep 05, 2008
Chemicals Used
4-Chlorobenzene-1-Carbohydrazide, 97% (Maybridge BB), Carbon disulphide, 99% (Aldrich), Potassium hydroxide (Aldrich), Ethanol (Merck) 99.9%.
Procedure
4-Chlorobenzene-1-carbohydrazide (15g, 0.088M) was dissolved in carbon disulphide (5.8ml, 0.097M) and alcoholic KOH (7.4g, 0.132M, KOH in 15ml ethanol) was added drop wise to at room temperature. The reaction mixture was stirred at room temperature using a magnetic stirrer for 6 hrs and monitored using thin layer chromatography (15:85; methanol:benzene). Filtration afforded N’-(4-chloro-benzoyl)hydrazine carbodithio potassium salt as yellow crystals. Yield: 22g, 87.85%.
Author's Comments
It is essential to add the alcoholic KOH to the reaction mixture drop wise to get the best results. The reaction has been carried out successfully on up to a 150g scale.
Data
1R (KBr, cm-1), 835 (C-S stretch) 721 (C-Cl stretch), 1HNMR (DMSO d6,) 7-7.8(m, 4H,Ar-H), 2.0 (s, 1H,NH), 8.0(s, 1H,NH), Mass spectra 284.83 (molecular ion peak)
Lead Reference
1.Udupi R H, Purushottamachar P, Bhat A R. Indian Journal of Heterocyclic Chemistry, 2000, 9, 291-294. 2.Udupi R H, Rajeeva, Srinivasalu N, Pasha T Y, Setty S R, Bhat A R. Indian Journal of Heterocyclic Chemistry, 2004, 13, 237-240.
Other References
1.Klimesova V, Zahajska L, et al. Farmaco, 2004, 59, 279-88. 2.Alanine A, Anselm L, et al. Bioorg. Med. Chem. Lett, 2004, 14, 817-21.
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Keywords: Hydrazine, Carbodithio Potassium Salt, addition, sulphides
