Ethyl benzoylacetate → HCID 135979769, compound

Temperature

90 °C

In a 250 mL RBF with a stirrer bar, a mixture of 3-oxo-3-phenyl-propionic acid ethyl ester (15 g, 78 mmol), K2CO3 (11.0 g, 80 mmol) and 2-imino-hexahydro-pyrimidin-5-ol hydrochloride (11.8 g, 78 mmol) in EtOH (150 mL) was heated at 90° C. under nitrogen overnight. After 17 h, the mixture was cooled to room temperature, and filtered. The mother liquid was concentrated to a sludge that was then diluted with H2O. The resulting slurry was filtered and the solid was washed first with MeOH, then a mixture of EtOAc-MeOH (2:1) to give the first batch of product. The solid residue from the crude reaction was washed first with H2O (3×10 mL), then MeOH, and finally a mixture of EtOAc-MeOH (2: 1) to yield a second batch of product. The combined products were the dried in air to provide a white solid. 1H NMR (400 MHz, DMSO6): 7.94 (m, 2 H), 7.44 (bt, J 3.2, 0.5 H), 6.10 (s, 1H), 5.35 (d, J 3.2, 0.5 H), 4.22 (m, 1 H), 4.12 (d, J 14,1H), 3.54 (dd, J 14, 2.0,1 H), 3.39 (d, 12.4, 1H), 3.18 (m, 1H). M+1: 244.

1. temperaturethe mixture was cooled to room temperature
2. filtrationfiltered
3. concentrationThe mother liquid was concentrated to a sludge that
4. additionwas then diluted with H2O
5. filtrationThe resulting slurry was filtered
6. washthe solid was washed first with MeOH
7. additiona mixture of EtOAc-MeOH (2:1)
8. customto give the first batch of product
9. customThe solid residue from the crude reaction
10. washwas washed first with H2O (3×10 mL)
11. additionMeOH, and finally a mixture of EtOAc-MeOH (2: 1)
12. customto yield a second batch of product
13. customdried in air
14. customto provide a white solid

ORD record

ord-53d91446c3054d59a42f9437d9e53686

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07504403B2