Sodium Hydroxide → HCID 56970895, compound

Temperature

130 °C

In a 100 mL round bottomed flask was placed stereo isomeric mixture of 4-(4-chlorophenyl)-2-pyridin-4-yl-5,6-dihydro-1-benzothiophen-7(4H)-one oxime prepared above and then was added polyphosphoric acid (11 g, 46 mmol) and the mixture was stirred for 6 h at 130° C. During this period, the mixture was occasionally mixed by hand. The mixture was allowed to cool to ambient temperature and then was added crushed ice (ca 20 ml) while the reaction mixture is hot. The mixture was stirred for 30 min at rt. A dark brown suspension was obtained, which was basicified by the addition of 5N NaOH (30 mL, pH ca 12). The mixture was extracted with a 1:1 mixture of CH2Cl2 and THF (30 mL×3). The combined organic phase was dried over anhydrous MgSO4. Insoluble materials were removed by filtration and the filtrate was concentrated under reduced pressure to obtain title compound (230 mg; 68%) as a yellowish off-white powder, which was only one isomer.

1. customIn a 100 mL round bottomed flask was placed
2. customprepared above
3. waitDuring this period
4. additionthe mixture was occasionally mixed by hand
5. temperatureto cool to ambient temperature
6. additionwas added
7. stirringThe mixture was stirred for 30 min at rt
8. customA dark brown suspension was obtained
9. extractionThe mixture was extracted with a 1:1 mixture of CH2Cl2 and THF (30 mL×3)
10. dry with materialThe combined organic phase was dried over anhydrous MgSO4
11. customInsoluble materials were removed by filtration
12. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-1b43b229341c4332a9d110bb05fe8fc0

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08765746B2