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Paper | Regular issue | Vol 29, No. 6, 1989, pp.1185-1189
Published online, 1st January, 1970
DOI: 10.3987/COM-89-4954
Facile Synthesis of 2-(5-Isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)phenyl Phosphonates

Hideyuki Takenaka and Yoshio Hayase

*Aburahi Laboratories, Shionogi & Co. Ltd., Gotanda, Koka-cho, Koka-gun, Shiga 520-3423, Japan


The synthesis of 2-(5-isopropyI-5-methyl-4-oxo-2-imidazoline-2-yl)phenyl phosphonates (3-5) from benzoyl chloride is described. The condensation between benzoyl chloride and 2-amino-2,3-dimethylbutanamide (10) afforded 5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl-benzene (11). Lithiation of 11 with sec-butyllithium, followed by reaction with diethyl chlorophosphate gave diethyl 2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)phenylphosphate (3). Treatment of 3 with bromotrimethylsilane afforded 4 and 2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)phenylphosphonic acid (5).