Formanilide → HCID 67125406, compound

Temperature

100 °C

A mixture of N-Formyl-aniline (8a, commercially available) (3.634 g, 30 mmol) and phosphorus pentasulfide (1.351 g, 3.04 mmol) in dry 1,4-dioxane (4 mL) was stirred at room temperature for 15 min under an argon atmosphere. 4-Chloro-2-butanone (2.131 g, 20 mmol) was added and the resulting slurry was heated at 100° C. The reaction mixture was refluxed for 50 min, initially becoming clear yellow and finally deep red. After cooling at room temperature, the crude mixture was diluted with H2O (20 mL). Na2CO3 was added to the reaction mixture until pH≈7. The solvent was evaporated under reduced pressure and the resulting solid was suspended in CH2Cl2 and purified by column chromatography (column packed with silica gel) eluting with EtOH/CH2Cl2 (15/85). Upon concentration of the last yellowish band, a viscous orange oil was obtained. This was solidified when washed under vigorous stifling with diethyl ether (3×2 mL) to afford 9a as a light pink solid (770 mg, 11%). 1H NMR (CD2Cl2, 300 MHz): δ=11.13 (s, 1H), 7.67-7.60 (m, 3H), 7.53-7.49 (m, 2H), 2.57 (s, 3H), 2.23 (s, 3H); 13C{1H} NMR (CD2Cl2, 75 MHz): δ=161.03, 142.08, 141.75, 137.19, 132.10, 130.84, 126.34, 13.10, 12.86; HRMS (FAB+) calculated for C11H12NS [M]+ 190.0690, observed 190.0693.

1. temperatureThe reaction mixture was refluxed for 50 min
2. temperatureAfter cooling at room temperature
3. customThe solvent was evaporated under reduced pressure
4. custompurified by column chromatography (column packed with silica gel)
5. washeluting with EtOH/CH2Cl2 (15/85)
6. customUpon concentration of the last yellowish band, a viscous orange oil was obtained
7. washwashed under vigorous stifling with diethyl ether (3×2 mL)

ORD record

ord-f41596d789a94f06aaa40d8e0d8a18e5

Source dataset

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08039566B2