A Versatile Procedure for the Preparation of Aryl Thiocyanates Using N-Thiocyanatosuccinimide (NTS)

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• 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.
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• 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.
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• Kugelrohr (short-path) distillation: temperature is that of the oven.
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