Methyl iodide → 3-bromo-4-methylbenzohydrazide

Step-3: 5-(3-Bromo-4-methylphenyl)-3-methyl-1,3,4-oxadiazol-2(3H)-one: A mixture of 5-(3-bromo-4-methylphenyl)-1,3,4-oxadiazol-2(3H)-one (400 mg, 1.57 mmol, 1.0 eq), methyl iodide (0.2 mL, 3.15 mmol, 2.0 eq) and potassium carbonate (210 mg, 3.15 mmol, 2.0 eq) in DMF (10 mL) was stirred at room temperature for 24 h. Water (50 mL) was added to the reaction mixture followed by ethyl acetate (30 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×20 mL). The combined organic layers were washed with water (2×25 mL), brine (20 mL), dried (Na2SO4) and filtered. The filtrate was concentrated under vacuum to afford 400 mg of the desired product as a white solid. 1HNMR (400 MHz, DMSO-d6) δ 7.90 (d, J=2.0 Hz, 1H), 7.70 (dd, J=8.0, 2.0 Hz, 1H), 7.54 (d, J=8.0 Hz, 1H), 3.40 (s, 3H), 2.41 (s, 3H); ESI-MS (m/z) 269, 271 [(MH)+, Br79,81].

1. customThe layers were separated
2. extractionthe aqueous layer was extracted with ethyl acetate (2×20 mL)
3. washThe combined organic layers were washed with water (2×25 mL), brine (20 mL)
4. dry with materialdried (Na2SO4)
5. filtrationfiltered
6. concentrationThe filtrate was concentrated under vacuum

ORD record

ord-ef2869e18b4141a9a460cab6df8d5cc7

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09169242B2