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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

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
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
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.
benzothiazoles, synthesis, x-ray crystal structures, ir, nmr spectroscopy
1024-1221
21-32
Drake, John E.
6de1350f-4eb6-4ca7-b796-947f4fec467d
Hursthouse, Michael B.
a65b4d35-2ea0-47e7-938a-d744f4d9ba28
Kriplani, Prashant
1aa04755-2326-4e84-a8f1-3b8ddfc6f3b2
Light, Mark E.
13b5eb33-3114-4fb7-8500-90ce69e9933c
Mithlesh, None
860fa3b2-9d18-4551-8075-9f1b4d395be1
Ojha, Krishan G.
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Pareek, Pawan K.
2c962b9c-f227-49ef-8ddf-ef8cfa8b219f
Ratnani, Raju
0a86c56f-00c6-4c9f-8aa0-52667938ba70
Drake, John E.
6de1350f-4eb6-4ca7-b796-947f4fec467d
Hursthouse, Michael B.
a65b4d35-2ea0-47e7-938a-d744f4d9ba28
Kriplani, Prashant
1aa04755-2326-4e84-a8f1-3b8ddfc6f3b2
Light, Mark E.
13b5eb33-3114-4fb7-8500-90ce69e9933c
Mithlesh, None
860fa3b2-9d18-4551-8075-9f1b4d395be1
Ojha, Krishan G.
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Pareek, Pawan K.
2c962b9c-f227-49ef-8ddf-ef8cfa8b219f
Ratnani, Raju
0a86c56f-00c6-4c9f-8aa0-52667938ba70

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).

Record type: Article

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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Published date: March 2009
Keywords: benzothiazoles, synthesis, x-ray crystal structures, ir, nmr spectroscopy

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Local EPrints ID: 67651
URI: http://eprints.soton.ac.uk/id/eprint/67651
ISSN: 1024-1221
PURE UUID: e64baab6-1899-47cb-8900-0bde15d1b33f

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Date deposited: 02 Sep 2009
Last modified: 19 Jul 2019 23:49

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Contributors

Author: John E. Drake
Author: Michael B. Hursthouse
Author: Prashant Kriplani
Author: Mark E. Light
Author: None Mithlesh
Author: Krishan G. Ojha
Author: Pawan K. Pareek
Author: Raju Ratnani

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