Water → HCID 22325512, compound

To absolute ethanol (200 ml), sodium (3.62 g, 157 mmol) was added at room temperature under nitrogen atmosphere. The reaction mixture as stirred until all the sodium had reacted. A solution of diethyl-(2-fluorophenyl)malonate (20 g, 78.7 mmol) in absolute ethanol (50 ml) was then added followed by thiourea (8.38 g, 110 mmol). The reaction mixture was then refluxed under nitrogen atmosphere for 17 hours. The cooled reaction mixture was then poured into water (800 ml), the reswiting mixture stirred for 15 minutes and extracted with diethyl ether (500 ml). The organic phase was extracted with brine (150 ml, ⅓ saturated) and the aqueous layers combined. Now concentrated hydrochloric acid (14 ml) was added to the aqueous phase and the resulting white suspension was stirred gently for 1 hour. The suspension was filtered and the resulting solid washed with water, followed by diethyl ether and dried in vacuo for approximately 12 hours to afford 8.59 g (46% yield) of the title compound as a white solid (melting point: >240° C.).

1. customhad reacted
2. temperatureThe reaction mixture was then refluxed under nitrogen atmosphere for 17 hours
3. customThe cooled reaction mixture
4. extractionextracted with diethyl ether (500 ml)
5. extractionThe organic phase was extracted with brine (150 ml, ⅓ saturated)
6. additionNow concentrated hydrochloric acid (14 ml) was added to the aqueous phase
7. stirringthe resulting white suspension was stirred gently for 1 hour
8. filtrationThe suspension was filtered
9. washthe resulting solid washed with water
10. customdried in vacuo for approximately 12 hours

ORD record

ord-8c0a0c77d65c4b918f5ddfb8394f68ea

Source dataset

uspto-grants-2005_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06943252B2