Water → 2-(1,3-Diphenyl-1H-1,2,4-triazol-5-yl)acetonitrile

HRID 1621152ノート

反応式

HRID 1621152 の反応式
Br[CH2:2][C:3]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:6]=[C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:4]=1.[C-:20]#[N:21].[K+].O>CS(C)=O>[C:8]1([N:7]2[C:3]([CH2:2][C:20]#[N:21])=[N:4][C:5]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:6]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

参加物

5

反応物 3

HCID 962WaterHCID 9032Potassium CyanideHCID 866774905-(Bromomethyl)-1,3-diphenyl-1H-1,2,4-triazole

生成物 1

HCID 131177802-(1,3-Diphenyl-1H-1,2,4-triazol-5-yl)acetonitrile収率 114.4%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
60 °C

実験手順

A mixture of 5-(bromomethyl)-1,3-diphenyl-1H-1,2,4-triazole (265 mg, 843 μmol) and potassium cyanide (62.3 mg, 928 μmol) in DMSO (5 mL) was heated at 60° C. for 1.5 h. The reaction mixture was cooled to RT, poured into water (25 mL) and extracted with ethyl acetate (2×50 mL). The organic phases were washed with water (2×25 mL) and brine (1×25 mL), and the combined organic layer was dried over MgSO4 and concentrated in vacuo to give 251 mg of crude product. The product was obtained after purification by flash chromatography (using silica gel and an ethyl acetate/heptane gradient) as light yellow waxy solid (120 mg, 461 μmol, 54.7%).

後処理

  1. temperatureThe reaction mixture was cooled to RT
  2. extractionextracted with ethyl acetate (2×50 mL)
  3. washThe organic phases were washed with water (2×25 mL) and brine (1×25 mL)
  4. dry with materialthe combined organic layer was dried over MgSO4
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-e3262c180684443d9049f7f3ab1c54a5
出典データセット
uspto-grants-2014_07
特許番号
US08772510B2

反応ノート

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