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

HRID 587280ノート

反応式

HRID 587280 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 74505Methyltriphenyliphosphonium bromide触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

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 room 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.

後処理

  1. customThe resultant reaction mixture
  2. customAfter completion of the reaction (TLC)
  3. temperaturethe reaction mixture was cooled to room 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)

出典と根拠

ORDレコード
ord-8764128c71374db9bd11560100b2301d
出典データセット
uspto-grants-2016_01
特許番号
US09226500B2

反応ノート

読み込み中…