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

HRID 967755ノート

反応式

HRID 967755 の反応式
C[N:2]([CH:4]=[N:5][C:6](=O)[CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)C.[CH3:16][NH:17]N>C(O)(=O)C>[CH3:16][N:17]1[C:6](/[CH:7]=[CH:8]/[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:5][CH:4]=[N:2]1

参加物

4

反応物 2

HCID 6061MethylhydrazineHCID 3745097N-[(Dimethylamino)methylene]-cinnamamide

生成物 1

HCID 222913301-methyl-5-[(E)-2-phenylethenyl]-1H-1,2,4-triazole収率 49%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
90 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-cbcf35d54abc4f11811a073a371914da
出典データセット
uspto-grants-2005_10
特許番号
US06956049B1

反応ノート

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