References
- Brewster , R. Q. and Schroeder , W. 1943 . Org. Synth. Coll. , Vol. II : 574
- Söderbäck , E. 1919 . Ann. Chem. , 419 : 217
- Kaufman , H. P. and Weber , E. 1929 . Arch. Pharm. , 267 : 201
- Kelly , T. R. , Kim , M. H. and Curtis , A. D.M. 1993 . J. Org. Chem. , 58 : 5855
- Kaufmann , H. P. and Küchler , K. 1934 . Ber. , 67 : 944
- Bacon , R. G.R. and Guy , R. G. 1960 . J. Chem. Soc. , : 318
- Wood , J. L. 1946 . Org. React. , 3 : 240
- Uemura , S. , Onoe , A. , Okazaki , H. and Okano , M. 1975 . Bull. Chem. Soc. Jpn. , 48 : 619
- Woodgate , P. D. , Lee , H. H. , Rutledge , P. S. and Cambie , R. C. 1976 . Tetrahedron Lett. , : 1531
- Maxwell , R. J. , Silbert , L. S. and Russell , J. R. 1977 . J. Org. Chem. , 42 : 1510
- Maxwell , R. J. and Silbert , L. S. 1978 . Tetrahedron Lett. , : 4991
- Treatment of N,N-dimethylaniline under otherwise identical conditions for 4 h at 25°C gave N,N-dimethyl-2,4-dithiocyanatoaniline, mp 75–76°C (from CH2Cl2:hexanes) in 95% yield. Spectral data (FTIR, 1H-NMR, MS) were in accord with expectation; HR-EIMS: found, 235.0231; calcd. for C10H9N3S2, 235.0238.
- Compound 10 had the expected spectral data and satisfactory elemental analysis (C,H, N, S; ±0.3%). It is also a useful synthetic intermediate, reacting very similarly to the thiocyanate 3 on treatment with reducing agents.
- Kugelrohr (short-path) distillation: temperature is that of the oven.