Hydrazine hydrate (1:1) → HCID 178434606, compound

HRID 967756Notes

Reaction equation

HRID 967756 reaction equation
CN([CH2:4][CH:5]=[N:6][C:7](=O)[CH:8]=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)C.O.[NH2:18][NH2:19]>C(O)(=O)C>[CH3:4][C:5]1[N:6]=[C:7](/[CH:8]=[CH:9]/[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[NH:19][N:18]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 69738220HCID 69738220, compound

Product 1

HCID 178434606HCID 178434606, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

N-[(Dimethylamino)ethylidene]-cinnamamide (2.0 g, 9.0 mmol) was added to a solution of hydrazine hydrate (0.59 mL, 10 mmol) and acetic acid (25 mL). The mixture was heated to 90° C. for 3 h, cooled, and concentrated in vacuo. The resulting material was basified (pH 8) with solid K2CO3, and partitioned between ethyl acetate and water. The organics were dried over Na2SO4 and concentrated in vacuo. The resultant material was purified by flash column chromatography on silica eluting with 1:2 hexane-ethyl acetate to afford 3-methyl-5-[(E)-2-phenylethenyl]-1H-1,2,4-triazole (1.6 g, 96% yield) as a white powder. M.p. 131–134° C. 1H NMR (CDCl3,300 MHz) δ 7.68 (d, J=16 Hz, 0.3H), 7.59 (d, J=16 Hz, 0.7H), 7.49 (m, 2H), 7.32 (m, 3H), 7.05 (d, J=16 Hz, 1H), 6.49 (d, J=16 Hz, 0.4H), 6.21 (br s, 0.3H), 5.88 (br s, 0.3H), 2.53 (s, 3H). MS (EI ionization) 184 (M+−H).

Workup

  1. temperaturecooled
  2. concentrationconcentrated in vacuo
  3. custompartitioned between ethyl acetate and water
  4. dry with materialThe organics were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe resultant material was purified by flash column chromatography on silica eluting with 1:2 hexane-ethyl acetate

Sources & evidence

ORD record
ord-f1e14335b37c4f9dae06c2159f65d072
Source dataset
uspto-grants-2005_10
Patent number
US06956049B1

Reaction notes

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