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

Drake, John E., Hursthouse, Michael B., Kriplani, Prashant, Light, Mark E., Mithlesh, None, Ojha, Krishan G., Pareek, Pawan K. and Ratnani, Raju (2009) 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. Main Group Chemistry, 8 (1), 21-32. (doi:10.1080/10241220902962911).

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 H-1 NMR spectroscopy. Two crystal structures were determined. ClC6H3(SCN)=NCHC6H4N(CH3)(2) crystallizes as triclinic, P-1, a = 5.8799(2), b = 15.9279(4), c = 16.7264(4) angstrom, alpha = 64.769(1)degrees, beta = 89.729(2)degrees, gamma = 88.047(1)degrees, V = 1416.15(7) angstrom(3), Z = 4, R = 0.0430, R-w = 0.1035. O2NC6H3(SCN)NH2 center dot OCHC6H4N(CH3)(2) crystallizes as monoclinic, P2/c, a = 18.7645(7), b = 3.8048(1), c = 22.0141(7) angstrom, beta = 94.743(2)degrees, V = 1566.32(9) angstrom(3), Z = 4, R = 0.0398, R-w = 0.0919.

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