Potassium Carbonate → 2-(3-nitro-1H-1,2,4-triazol-1-yl)-5-vinylbenzonitrile

HRID 1502899노트

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HRID 1502899 반응식
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([N:11]2[CH:15]=[N:14][C:13]([N+:16]([O-:18])=[O:17])=[N:12]2)=[C:7]([CH:10]=1)[C:8]#[N:9])=O.[C:19]([O-])([O-])=O.[K+].[K+]>O1CCOCC1.[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[N+:16]([C:13]1[N:14]=[CH:15][N:11]([C:6]2[CH:5]=[CH:4][C:3]([CH:1]=[CH2:19])=[CH:10][C:7]=2[C:8]#[N:9])[N:12]=1)([O-:18])=[O:17]

참가 물질

5

반응물 2

HCID 11430Potassium CarbonateHCID 866752155-formyl-2-(3-nitro-1H-1,2,4-triazol-1-yl)benzonitrile

생성물 1

HCID 866752162-(3-nitro-1H-1,2,4-triazol-1-yl)-5-vinylbenzonitrile수율 70%

시약·촉매·용매 2

HCID 74505Methyltriphenyliphosphonium bromide촉매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

To a stirred solution of 5-formyl-2-(3-nitro-1H-1,2,4-triazol-1-yl)benzonitrile (0.36 g, 1.49 mmol) in 1,4-dioxane (25 mL), were added K2CO3 (0.3 g, 2.2 mmol) and methyl triphenyl phosphonium bromide (0.63 g, 1.79 mmol). The resultant reaction mixture was heated to 100° C. for 18 h. After completion of the reaction (TLC), the reaction mixture was cooled to ambient temperature and filtered and the obtained filtrate was concentrated under reduced pressure. Purification by flash chromatography (SiO2, 100-200 mesh; 25-30% EtOAc in petroleum ether) to afford the title compound as a solid (0.25 g, 70%): mp 103-105° C.; 1H NMR (400 MHz, DMSO-d6) δ 9.50 (s, 1H), 8.34 (m, 1H), 7.98 (d, J=7.8 Hz, 1H), 7.68 (d, J=7.8 Hz, 1H), 6.87 (m, 1H), 6.20 (d, J=15.7 Hz, 1H), 5.56 (d, J=11.8 Hz, 1H); ESIMS m/z 240.27 ([M−H]−); IR (thin film) 2240, 1514, 1312 cm−1.

후처리

  1. customThe resultant reaction mixture
  2. customAfter completion of the reaction (TLC)
  3. temperaturethe reaction mixture was cooled to ambient temperature
  4. filtrationfiltered
  5. concentrationthe obtained filtrate was concentrated under reduced pressure
  6. customPurification by flash chromatography (SiO2, 100-200 mesh; 25-30% EtOAc in petroleum ether)

출처 및 근거

ORD 기록
ord-6853e3233d9a4b4a83ab350c6228fdd0
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09211280B2

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