Preparation of Arylthiocyanates Using N,N′-Dibromo-N,N′-bis(2,5-dimethylbenzenesulphonyl) ethylenediamine and N,NDibromo-2,5-dimethylbenzenesulphonamide in the Presence of KSCN as a Novel Thiocyanating Reagent
Abstract
:Introduction
Result and Discussion
Substrate | Temp(°C)/ time(h) | Solvent | N-bromo reagent | Product | % Yield |
---|---|---|---|---|---|
N,N-Dimethylaniline | 0/3 | MeOH | A | 1 | 98 |
Anisole | 25/4 | HOAc | B | 2a | 275 |
Mesitylene | 0/2 | MeOH | A | 3 | 96 |
Cumene | 0/2 | MeOH | B | 4 | 80 |
Thiophene | 25/4 | HOAc | A | 5 | 70 |
Benzene | 25/2 | HOAc | A,B | − | − |
Experimental
General
References and Notes
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- Kaufmann, H. P.; Kuchler, K. Ber. 1934, 67, 944.
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- Wood, J. L. Org. React. 1946, 3, 240.
- (a) Uemura, S.; Onoe, A.; Okazaki, H.; Okano, M. Bull. Chem. Soc. Jpn. 1975, 48, 619. (b) Woodgate, P. D.; Lee, H. H.; Rutledge, P. S.; Cambie, R. C. Tetrahedron Lett. 1976, 1531.
- Dean, T. F.; De Stefano, V.; Ian, Still, W. J. Synth. Commun. 1995, 25, 1277.
- Khazaei, A.; Shirdarreh, A. Synth. Commun. 1999, 29, 4079.
- Treatment of N,N-dimethyaniline under otherwise identical conditions for 4 h at 25°C gave N,N′- dimethyl-2,4-dithiocyanatoaniline (95%), mp. 75-76°C (CH2Cl2/hexane); spectral data (FTIR, 1H- NMR) were in accord with expected values.
- Samples Availability: Not available
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Khazaei, A.; Alizadeh, A.; Vaghei, R.G. Preparation of Arylthiocyanates Using N,N′-Dibromo-N,N′-bis(2,5-dimethylbenzenesulphonyl) ethylenediamine and N,NDibromo-2,5-dimethylbenzenesulphonamide in the Presence of KSCN as a Novel Thiocyanating Reagent. Molecules 2001, 6, 253-257. https://doi.org/10.3390/60300253
Khazaei A, Alizadeh A, Vaghei RG. Preparation of Arylthiocyanates Using N,N′-Dibromo-N,N′-bis(2,5-dimethylbenzenesulphonyl) ethylenediamine and N,NDibromo-2,5-dimethylbenzenesulphonamide in the Presence of KSCN as a Novel Thiocyanating Reagent. Molecules. 2001; 6(3):253-257. https://doi.org/10.3390/60300253
Chicago/Turabian StyleKhazaei, Ardeshir, Abdolhamid Alizadeh, and Ramin Ghorbani Vaghei. 2001. "Preparation of Arylthiocyanates Using N,N′-Dibromo-N,N′-bis(2,5-dimethylbenzenesulphonyl) ethylenediamine and N,NDibromo-2,5-dimethylbenzenesulphonamide in the Presence of KSCN as a Novel Thiocyanating Reagent" Molecules 6, no. 3: 253-257. https://doi.org/10.3390/60300253