Methylhydrazine → 1-methyl-5-[(E)-2-phenylethenyl]-1H-1,2,4-triazole

Temperature

90 °C

N-[(Dimethylamino)methylene]-cinnamamide (2.0 g, 10 mmol) was added to a mixture of acetic acid (20 mL) and methylhydrazine (0.6 mL, 11 mmol). The mixture was heated to 90° C. for 2 h. The cooled mixture was concentrated in vacuo, and made basic (pH 9) with solid K2CO3. The aqueous residue was partitioned between ethyl acetate and water, the organics were dried over Na2SO4, and concentrated in vacuo. The resultant powder was recrystallized from a minimum of boiling Ethyl acetate. The collected solids were triturated and washed with ethyl acetate to afford 1-methyl-5-[(E)-2-phenylethenyl]-1H-1,2,4-triazole (0.9 g, 49% yield) as a pale yellow powder. M.p. 67–70° C. from Ethyl acetate. 1H NMR (CDCl3, 300 MHz) δ 7.88 (s, 1H), 7.73 (d, J=16 Hz, 1H), 7.57 (m, 2H), 7.39 (m, 3H), 6.92 (d, J=16 Hz, 1H), 3.96 (s, 3H).

1. concentrationThe cooled mixture was concentrated in vacuo
2. customThe aqueous residue was partitioned between ethyl acetate and water
3. dry with materialthe organics were dried over Na2SO4
4. concentrationconcentrated in vacuo
5. customThe resultant powder was recrystallized from a minimum of boiling Ethyl acetate
6. customThe collected solids were triturated
7. washwashed with ethyl acetate

ORD record

ord-cbcf35d54abc4f11811a073a371914da

Source dataset

uspto-grants-2005_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06956049B1