Abstract
1,3-dichloro-5,5-dimethylhydantoin (DCH) and 1,3-dibromo-5,5-dimethylhydantoin (DBH) were used as effective oxidizing agents for the oxidation of urazoles and bis-urazoles to their corresponding triazolinediones under mild conditions at room temperature with good to excellent yields.
Key words
1,3-dichloro-5,5-dimethylhydantoin (DCH) - 1,3-dibromo-5,5-dimethylhydantoin (DBH) - urazoles - bis-urazoles - triazolinediones
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36 Chemicals were purchased from Fluka, Merck, Riedel-De Haen AG and Aldrich chemical companies. Yields refer to isolated pure products. The oxidation products were characterized by comparison of their spectral (IR, UV, 1 H NMR, and 13 C NMR) and physical data with authentic samples. Silica sulfuric acid (III ) was prepared according to our previously reported procedure.
[35 1 4 5
37
Oxidation of 4-Chlorophenyl Urazole (
1g) to 4-Chloro-phenyl-1,2,4-triazoline-3,5-dione (
2g) with DBH. A Typical Procedure.
1g (0.212 g, 1 mmol) and DBH (0.286 g, 1 mmol) in CH2 Cl2 (15 mL) was stirred at r.t. for 2 h. Silica sulfuric acid (0.5 g) was added to the reaction mixture and stirred for 15 min. Then the reaction mixture was filtered and the CH2 Cl2 removed to give a red crystalline solid 2g (0.205 g, 92% yield), mp 132-135 °C [lit.
[3 2 Cl2 , some of TADs are lost with solvent.
