Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Urea | HCID 1176 | — |
| Reactant | 2-Phenylacetophenone | HCID 9948 | — |
| Reactant | 3-Formyl-2-hydroxybenzonitrile | HCID 20554650 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Product | HCID 56961407 | HCID 56961407 | — |
Reaction Steps
To a solution of 1,2-diphenylethanone (1.6 g, 8.16 mmol), and 3-formyl-2-hydroxybenzonitrile (Intermediate 47b) (1.0 g, 6.80 mmol) in AcOH (5 mL) was added urea (1.2 g, 20.4 mmol). The mixture was stirred at 120° C. under microwave for 3 h. The volatiles were removed under reduced pressure and standard aqueous workup procedure was followed. The crude was recrystallized by EA (10 mL) to afford Compound 94 as a white power (436 mg, 26%). 1H NMR (DMSO-d6 500 MHz): δ 8.10 (s, 1H), 7.79 (d, J=2.5 Hz, 1H), 7.75 (d, J=2.0 Hz, 1H), 7.58 (d, J=7.5 Hz, 3H), 7.30-7.36 (m, 3H), 7.18 (s, 1H), 7.02 (d, J=6.0 Hz, 3H), 6.78 (d, J=6.0 Hz, 2H), 4.44 (d, J=2.0 Hz, 1H), 4.14 (s, 1H); MS (ESI): m/z 368.1 [M+1]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08741915B2 |
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| Source dataset | uspto-grants-2014_06 |
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| ORD ID | ord-cbafa899a75c431591f53b58a6ff9326 |
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| Source note | uspto-grants-2014_06 |
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