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

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) ų, Z = 4, R = 0.0430, R_w = 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) ų, Z = 4, R = 0.0398, R_w = 0.0919.