1,3-Dichloro-5,5-dimethylhydantoin → HCID 86723404, compound

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Reaction Steps

Using the procedure for Example 15, 4-amino-6-cyclobutyl-5-fluoropicolinaldehyde (0.5 g, 2.57 mol), 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione (0.279 g, 1.416 mol) and CH3CN (26 mL) gave 4-amino-3-chloro-6-cyclobutyl-5-fluoropicolinaldehyde (289 mg, 45.7%) as a red foam: 1H NMR (400 MHz, CDCl3) δ 10.09 (s, 1H), 4.77 (d, J=9.4 Hz, 2H), 3.87 (ttdd, J=9.3, 8.3, 2.3, 1.1 Hz, 2H), 2.49 (m, 2H), 2.30 (m, 2H), 2.10 (m, 1H), 1.95 (tddd, J=13.4, 7.1, 3.5, 2.1 Hz, 1H); 19F NMR (376 MHz, CDCl3) δ −140.24; 13C NMR (101 MHz, CDCl3) δ 191.04, 149.06, 147.71, 145.14, 142.84, 139.20, 115.84, 35.24, 26.86, 18.62; EIMS m/z 228.

Provenance & Evidence