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

HRID 587278ノート

反応式

HRID 587278 の反応式
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]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 27695822-Fluoro-5-formylbenzonitrileHCID 178526901HCID 178526901、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f3d381a6743241d29d30e5a2b0b6d219
出典データセット
uspto-grants-2016_01
特許番号
US09226500B2

反応ノート

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