Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Urea | HCID 1176 | — |
| Reactant | 2-Phenylacetophenone | HCID 9948 | — |
| Reactant | 3-Carboxybenzaldehyde | HCID 12077 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 56961405 | HCID 56961405 | 15.1% |
Reaction Steps
To a solution of 1,2-diphenylethanone (784 mg, 4.0 mmol), 3-formylbenzoic acid (500 mg, 3.33 mmol) and urea (600 mg, 10.0 mmol) in EtOH (40 mL) was added concentrated HCl (1.6 mL). The mixture was stirred at 85° C. for 3 days. The volatiles were removed under reduced pressure and standard aqueous/EtOAc workup procedure was followed. Purification by column chromatography (100% EA) gave Compound 93 as an off-white powder (186 mg, 15%). 1H NMR (DMSO-d6 500 MHz): δ 8.70 (s, 1H), 7.99 (s, 1H), 7.83 (d, J=7.5 Hz, 1H), 7.57 (s, 2H), 7.50 (t, J=14.5 Hz, 1H), 7.21-7.25 (m, 5H), 6.79-7.02 (m, 3H), 6.78 (d, J=7.0 Hz, 2H), 5.24 (d, J=2.0 Hz, 1H); MS (ESI): m/z 371.1 [M+1]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09067893B2 |
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| Source dataset | uspto-grants-2015_06 |
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| ORD ID | ord-a750c80a96264852809f7aadb8e49714 |
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| Source note | uspto-grants-2015_06 |
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