Hydrazine hydrate (1:1) → HCID 178433092, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(5-acetyl-4-methylthiazol-2-yl)-3-(4-fluorobenzyl)-imidazolidin-2-one (0.33 g, 1.00 mmol) in N,N-dimethylformamide (10 mL) was added N,N-dimethylformamide dimethyl acetal (0.25 mL, 1.88 mmol). The reaction mixture was heated for 7 hours at 110° C., followed by the addition of hydrazine monohydrate (0.30 mL, 6.18 mmol). The reaction mixture was heated for another 10 minutes at 110° C., and concentrated in vacuo. The residue was washed with water and triturated with ethyl acetate to afford the title compound in 61% yield (0.22 g): mp 239-242° C. (ethyl acetate); 1H NMR (300 MHz, DMSO-d6) δ 12.90 (br s, 1H), 7.76 (br s, 1H), 7.35-7.31 (m, 2H), 7.19-7.13 (m, 2H), 6.42 (d, J=2.1 Hz, 1H), 4.39 (s, 2H), 3.98-3.93 (m, 2H), 3.44-3.38 (m, 2H), 2.36 (s, 3H), 2.24 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 163.6, 160.4, 155.7, 144.0, 142.5, 133.2, 130.4, 118.1, 116.0, 115.7, 103.2, 46.6, 42.4, 42.0, 16.9; MS (ES+) m/z 358.2 (M+1).

Provenance & Evidence