Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Magnesium | HCID 5462224 | — |
| Reactant | HCID 86645371 | HCID 86645371 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 178512072 | HCID 178512072 | 78.4% |
Reaction Steps
To a solution of (S)—N-(3-(4-(4-chlorophenoxy)phenyl)-1-tosyl-4-(3-(trifluoromethyl)-phenyl)imidazolidin-2-ylidene)cyanamide (1.06 g, 1.73 mmol) in MeOH (17 mL) is added magnesium powder (0.42 g, 17.3 mmol). The reaction mixture is heated to reflux for 45 min. After cooling down to room temperature, the mixture is quenched with saturated NH4Cl aqueous solution (150 mL) and extracted with EtOAc (3×75 mL). The combined organic layer is washed with brine, dried over MgSO4, concentrated, and purified by silica gel chromatography (20˜70% EtOAc/Hexanes) to provide the title compound (0.62 g, 78% yield) as a white solid product; 1H NMR (CDCl3, 400 MHz) δ 7.60 (m, 1H), 7.51 (m, 3H), 7.27 (d, 2H), 7.15 (d, 2H), 6.88 (m, 4H), 6.65 (br, 1H), 5.40 (dd, 1H), 4.21 (t, 1H), 3.63 (dd, 1H); HPLC-MS calculated for C23H16ClF3N4O (M+H+) 457.1, found 457.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08431607B2 |
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| Source dataset | uspto-grants-2013_04 |
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| ORD ID | ord-f742038186fd4bd3a153c1b0a83dd256 |
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| Source note | uspto-grants-2013_04 |
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