Facile synthesis of novel 2-(4′-N,N-dimethylbenzylidenoimino)-6-substituted-1,3-benzothiazoles and crystal structures of 2-(4′-N,N-dimethylbenzylidenoimino)-6-chloro-1,3-benzothiazole and the co-crystal of 2-amino-6-nitro-1,3-benzothiazole and 4-(N,N-dimethylamino)benzaldehyde

Article type: Research Article

Authors: Drake, John E. | Hursthouse, Michael B. | Kriplani, Prashant | Light, Mark E. | Mithlesh, | Ojha, Krishan G. | Pareek, Pawan K. | Ratnani, Raju

Affiliations: Department of Chemistry and Biochemistry, University of Windsor, Windsor, Ontario, N9B 3P4 Canada | Department of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, UK | Department of Pure & Applied Chemistry, M.D.S. University, Ajmer 305 009, India

Note: [] Corresponding author. Email: [email protected]

Abstract: 2-Amino-6-substituted-1,3-benzothiazoles were condensed with N,N-dimethylaminobenzaldehyde to give novel 2-(4′-N,N-dimethylbenzylidenoimino)-6-substituted-1,3-benzothiazoles in good yields. However, in the case of 2-amino-6-nitro-1,3-benzothiazole, the desired product 2-(4′-N,N-dimethylbenzylidenoimino)-6-nitro-1,3-benzothiazole was not observed. Products were characterized by elemental analysis and infrared (IR) and 1H NMR spectroscopy. Two crystal structures were determined. ClC6H3(SCN)N == CHC6H4N(CH3)2 crystallizes as triclinic, P-1, a = 5.8799(2), b = 15.9279(4), c = 16.7264(4) Å, α = 64.769(1)°, β = 89.729(2)°, γ = 88.047(1)°, V = 1416.15(7) Å3, Z = 4, R = 0.0430, Rw = 0.1035. O2NC6H3(SCN)NH2·OCHC6H4N(CH3)2 crystallizes as monoclinic, P2/c, a = 18.7645(7), b = 3.8048(1), c = 22.0141(7) Å, β = 94.743(2)°, V = 1566.32(9) Å3, Z = 4, R = 0.0398, Rw = 0.0919.

Keywords: benzothiazoles, synthesis, X-ray crystal structures, IR, NMR spectroscopy

DOI: 10.1080/10241220902962911

Journal: Main Group Chemistry, vol. 8, no. 1, pp. 21-32, 2009