Thiourea → HCID 86667467, compound

In a 100 mL round bottomed flask were placed ethyl 2-bromo-4-(4-chlorophenyl)-3-oxobutanoate (990 mg, 3.1 mmol) and isopropyl alcohol (20 mL). To the mixture was added thiourea (590 mg, 7.8 mmol) and the reaction was then refluxed for 16 h with stirring. The mixture was allowed to cool to rt and was then concentrated under reduced pressure. The residue was suspended in EtOAc (50 mL) and then washed with a saturated aqueous solution of NaHCO3 (50 mL), brine (50 mL), and dried over anhydrous MgSO4. Insoluble materials were removed by filtration and the filtrate was concentrated under reduced pressure. The residual off-white yellowish crystalline solid was essentially pure by LCMS and was used in the next step without further purification. LC/MS (FA) ES+ 296. 1H NMR (d6-DMSO, 400 MHz): δ: 7.80 (2H, br s), 7.32 (2H, d, J=8.8 Hz), 7.23 (2H, d, J=8.8 Hz), 4.14-4.20 (4H, m), 1.22 (3H, t, J=7.1 Hz).

1. customIn a 100 mL round bottomed flask were placed
2. temperaturethe reaction was then refluxed for 16 h
3. concentrationwas then concentrated under reduced pressure
4. washwashed with a saturated aqueous solution of NaHCO3 (50 mL), brine (50 mL)
5. dry with materialdried over anhydrous MgSO4
6. customInsoluble materials were removed by filtration
7. concentrationthe filtrate was concentrated under reduced pressure
8. customwas used in the next step without further purification

ORD record

ord-8cefbeea3b4b42dfb0732213102299a6

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08796271B2