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On the purity of 2‐[ ortho ‐anilinyl]‐1,3‐benzoxazole derived from 2 H ‐3,1‐benzoxazine‐2,4(1 H )dione ( isatoic anhydride ) [1,2]
Author(s) -
Button Karen M.,
Gossage Robert A.,
Jenkins Hilary A.,
Mahdi Tayseer,
Resanović Sanja
Publication year - 2010
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.326
Subject(s) - benzoxazole , chemistry , orthorhombic crystal system , molecule , crystal structure , lewis acids and bases , crystallography , crystal (programming language) , stereochemistry , medicinal chemistry , catalysis , organic chemistry , computer science , programming language
The Lewis acid catalyzed synthesis and chromatographic purification of isatoic anhydride‐derived 2‐(2′‐anilinyl)‐1,3‐benzoxazole ( 2 ) can result in the co‐isolation of 2 and a light pink colored impurity (<5%). This latter species has been identified (NMR, single crystal X‐ray diffraction, mp) as 2′‐hydroxy‐2‐aminobenzanilide ( 3 ), which represents a predictable intermediate in the formation of 2 . Compound 3 crystallizes in an orthorhombic crystal system of space group P 2 1 2 1 2 1 with four molecules in the unit cell (α = β = γ = 90°; a = 6.715 (2) Å, b = 12.100 (4) Å, c = 13.321 (4) Å; V = 1082.2 (6) Å 3 ). Pure 2 is characterized as a colorless, high‐melting solid; unlike the dark colored oil that is isolated if 2 contains traces of 3 . J. Heterocyclic Chem., (2010).