Hydrochloric Acid → 4-[4-[(E)-C-methyl-N-prop-2-ynoxycarbonimidoyl]phenyl]-1,2,4-triazolidine-3,5-dione
Reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14](=[O:15])[NH:13][NH:12][C:11]2=[O:16])=[CH:6][CH:5]=1)(=O)[CH3:2].Cl.[CH2:18]([O:21][NH2:22])[C:19]#[CH:20].Cl.O1CCOCC1>C(O)C>[CH2:18]([O:21]/[N:22]=[C:1](/[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14](=[O:15])[NH:13][NH:12][C:11]2=[O:16])=[CH:6][CH:5]=1)\[CH3:2])[C:19]#[CH:20]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To 4-(4-acetylphenyl)-1,2,4-triazolidine-3,5-dione (500 mg, 2.281 mmol) in ethanol (6.912 mL) was added O-(prop-2-ynyl)hydroxylamine hydrochloride (368 mg, 3.42 mmol) and HCl 4N in dioxane (1.711 mL, 6.84 mmol). The mixture was stirred at 50° C. for 2 hours and then concentrated in vacuo. Saturated sodium bicarbonate was added, extracted with ethyl acetate twice, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (60-100% ethyl acetate/heptane, and then 5% MeOH/ethyl acetate) giving (E)-4-(4-(1-(prop-2-ynyloxyimino)ethyl)phenyl)-1,2,4-triazolidine-3,5-dione (I-6a: 46 mg, 7%) as a white solid. LC-MS (M+1) 273.1, t=0.81 minute. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.23 (s, 3 H) 3.48 (t, J=2.40 Hz, 1 H) 4.80 (d, J=2.27 Hz, 2 H) 7.53 (d, J=8.59 Hz, 2 H) 7.76 (d, J=8.59 Hz, 2 H) 10.52 (s, 2 H).
Workup
- concentrationconcentrated in vacuo
- additionSaturated sodium bicarbonate was added
- extractionextracted with ethyl acetate twice
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by silica gel chromatography (60-100% ethyl acetate/heptane
Sources & evidence
- ORD record
- ord-1c7eb597c17942dda48f57c4948b7aad
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09149541B2
Reaction notes
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