Dimethylformamide → 4-[2-(Dimethylamino)ethenyl]-3-nitrobenzonitrile

HRID 1836646ノート

反応式

HRID 1836646 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([CH3:12])[CH:7]=[CH:8][C:9]=1[C:10]#N)([O-:3])=[O:2].[CH3:13][N:14]([CH:16]=O)[CH3:15].C[NH:19]C.CN(C)C=O>O>[CH3:13][N:14]([CH3:16])[CH:15]=[CH:10][C:9]1[CH:8]=[CH:7][C:6]([C:12]#[N:19])=[CH:5][C:4]=1[N+:1]([O-:3])=[O:2]

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 962352-Nitro-4-toluonitrileHCID 86587686HCID 86587686、化合物

生成物 1

HCID 8941414-[2-(Dimethylamino)ethenyl]-3-nitrobenzonitrile収率 74%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
110 °C

実験手順

A mixture of 3-nitro-p-tolunitrile (30.0 g, 185 mmol), DMF (100 mL), and dimethylformamide dimethylamine (24.3 g, 204 mmol) was heated to 110° C. for 16 h. The deep red solution was poured into H2O (1L) and extracted with EtOAc (4×250 mL). The organic layers were washed with H2O, brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The solid residue was triturated with hexanes to give 4-(2-dimethylamino-vinyl)-3-nitro-benzonitrile (28.5 g, 74%) after filtration. 1H NMR (400 MHz, DMSO-d6) 8.22 (1H, s), 7.83 (2H, m), 7.65 (1H, m), 5.67 (1H, d, J=13 Hz), 2.98 (6H, s); MS m/e 219 (M+H)+. Anal calcd. for C11H11N3O2: C, 60.82; H, 5.10; N, 19.34. Found: C, 60.54; H, 4.99; N, 19.40.

後処理

  1. extractionextracted with EtOAc (4×250 mL)
  2. washThe organic layers were washed with H2O, brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe solid residue was triturated with hexanes

出典と根拠

ORDレコード
ord-6cdabc9331554c629165c593af381238
出典データセット
uspto-grants-2004_08
特許番号
US06777437B2

反応ノート

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