Water → HCID 59838438, compound

Temperature

25 °C

To a suspension of 60% NaH (5.93 g, 247.08 mmol) in DMF (80 mL) taken in a one liter 2 neck round bottom flask fitted with a pressure equalizing addition funnel and a septum was added a solution of p-aminoacetophenone (20 g, 148.1 mmol) in DMF (60 mL) in drops through the pressure equalizing addition funnel under nitrogen atmosphere at 0° C. and the contents were stirred for 2 hours at 25° C. Then to the stirred solution was added 1,2-dibromoethane (97.48 g, 518.5 mmol) in drops and the contents were further stirred for another 18 hours at 90° C. The reaction mixture was cooled to 25-35° C. and was carefully added to cold water (650 mL) while stirring. The organics were extracted with ethylacetate (3×200 mL) and combined organics were washed with water (2×100 mL) followed by a brine wash. The separated organics were dried over Na2SO4 and concentrated under reduced pressure. The crude was chromatographed over silicagel by using 15-20% ethyl acetate/pet. ether (3 Lit), affording the title compound 5.1 g (14%) as a pale yellow solid. Mp: 92-94° C.

1. customfitted with a pressure
2. additionaddition funnel
3. additionaddition funnel under nitrogen atmosphere at 0° C.
4. stirringthe contents were further stirred for another 18 hours at 90° C
5. temperatureThe reaction mixture was cooled to 25-35° C.
6. stirringwhile stirring
7. extractionThe organics were extracted with ethylacetate (3×200 mL)
8. washcombined organics were washed with water (2×100 mL)
9. washwash
10. dry with materialThe separated organics were dried over Na2SO4
11. concentrationconcentrated under reduced pressure
12. customThe crude was chromatographed over silicagel

ORD record

ord-5f2f31dc0dfa4639ad894dddce15957c

Source dataset

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07456288B2