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

HRID 587749노트

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HRID 587749 반응식
F[C:2]1[CH:9]=[CH:8][C:7]([CH:10]=[O:11])=[CH:6][C:3]=1[C:4]#[N:5].C([O-])([O-])=O.[K+].[K+].[N+:18]([C:21]1[N:25]=[CH:24][NH:23][N:22]=1)([O-:20])=[O:19]>CN(C=O)C.O>[CH:10]([C:7]1[CH:8]=[CH:9][C:2]([N:23]2[CH:24]=[N:25][C:21]([N+:18]([O-:20])=[O:19])=[N:22]2)=[C:3]([CH:6]=1)[C:4]#[N:5])=[O:11]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 27695822-Fluoro-5-formylbenzonitrileHCID 178526901HCID 178526901, 화합물

생성물 1

HCID 866752155-formyl-2-(3-nitro-1H-1,2,4-triazol-1-yl)benzonitrile수율 45%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a stirring solution of 2-fluoro-5-formylbenzonitrile (0.5 g, 3.3 mmol) in DMF (25 mL) were added K2CO3 (0.68 g, 4.95 mmol) and 3-nitro-1,2,4 triazole (0.45 g, 4.2 mmol) and the resultant reaction mixture was stirred at ambient temperature for 14 h. After completion of reaction (TLC), the reaction mixture was diluted with water and extracted with EtOAc. The combined EtOAc layer was washed with water and brine then dried over Na2SO4 and concentrated under reduced pressure to afforded the title compound as a pale yellow solid (0.36 g, 45%): mp 170-172° C.; 1H NMR (300 MHz, DMSO-d6) δ 10.12 (s, 1H), 9.61 (s, 1H), 8.69 (s, 1H), 8.45 (d, J=9.3 Hz, 1H), 8.23 (d, J=9.3 Hz, 1H); ESIMS m/z 242.3 ([M−H]−); IR (thin film) 2238, 1705, 1551, 1314 cm−1.

후처리

  1. customthe resultant reaction mixture
  2. customAfter completion of reaction (TLC)
  3. extractionextracted with EtOAc
  4. washThe combined EtOAc layer was washed with water and brine
  5. dry with materialthen dried over Na2SO4
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-639398c64b4d42858e2986500fdc9cc6
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09226501B2

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