N,N'</i>-bis[(3,4-Dichlorophenyl)methyl]ethanediamide

Molecules 1997, 2, M3

N,N'-bis[(3,4-Dichlorophenyl)methyl]ethanediamide

Shu-Kun Lin*

Ciba-Geigy Limited, Pharmaceuticals Division, CH-4002 Basel, Switzerland

*Present Address: Molecular Diversity Preservation International (MDPI), Saengergasse 25, CH-4054 Basel, Switzerland. Tel. +41 79 322 3379, Fax +41 61 302 8918 ([email protected])

Received: 15 January 1997 / Published: 15 April 1997

A solution of K₂CO₃(2.39g, 17.3 mmol) in water (5 ml) was added to a mixture of N-(3,4-dichlorophenyl)methyl oxamic acid ethyl ester [1] (0.955 g, 3.46 mmol), 3,4-dichlorobenzylamonium chloride (1.0504 g, 3.80 mmol) in diethyl ether (100 ml) and stirred at r.t. overnight. The suspension was dissolved with EtOAc (80ml). The mixture was washed with HCl (0.001N, 100ml) water (2x100ml) and quickly dried (Na₂SO₄). A white precipitate formed after standing at r.t. Yield 0.1g (7%) of a white solid.

M.p. 213-214deg.C.

¹H-NMR ((D₆)DMSO): 9.41 (t, 2H, NH); 7.58 (d, 1H, HC(6)); 7.52 (d, 1H, HC(2)); 7.25 (q, 1H, HC(5)); 4.32 (d, 4H, CH₂).

MS: 404 (M⁺, containing 4Cl); 245, 174, 159.

Acknowledgments: The author would like to thank Dr. Vittorio Rasetti for his support.

References

1. Lin, S. -K. N-(3,4-Dichlorophenyl)methyl oxamic acid ethyl ester. Molecules 1997, 2, M2.

Sample Availability: Not available.