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

HRID 1621152노트

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HRID 1621152 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
60 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-e3262c180684443d9049f7f3ab1c54a5
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772510B2

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