Hydrochloric Acid → HCID 67321093, compound

A solution of 3-chloro-4-(bromoacetyl)nitrobenzene (546 mg, 1.96 mmol) and thioacetamide (162 mg, 2.15 mmol) in absolute EtOH (8 mL) was stirred at 85° C. for 1 h and cooled to room temperature. Solvent was evaporated in vacuo. A suspension of SnCl2.2H2O (1.46 g, 6.47 mmol) and conc. HCl (2 mL) in absolute EtOH (12 mL) was heated to reflux and the resulting clear solution was added to the residue. The reaction mixture was stirred at reflux for 1 h, cooled to room temperature and poured into a solution of KOH (4.4 g) in water (50 mL) at 0° C. The aqueous layer was extracted with EtOAc (3×) and the combined organics were dried over MgSO4, filtered, and concentrated in vacuo to give 438 mg of the titled product as a dark yellow oil (quant. yield): 1H NMR (400 MHz, DMSO-d6) δ 2.70 (s, 3H), 5.61 (broad s, 2H), 6.59 (dd, 1H), 6.69 (d, 1H), 7.58 (d, 1H), 7.62 (s, 1H); [M+H+]+ m/z 225.

1. customSolvent was evaporated in vacuo
2. temperaturewas heated
3. temperatureto reflux
4. additionthe resulting clear solution was added to the residue
5. temperatureat reflux for 1 h
6. temperaturecooled to room temperature
7. extractionThe aqueous layer was extracted with EtOAc (3×)
8. dry with materialthe combined organics were dried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated in vacuo

ORD record

ord-8bfb21bf57834b3b99eda87bfec2f7f5

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09174949B2