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

HRID 1836646노트

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HRID 1836646 반응식
[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]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 962352-Nitro-4-toluonitrileHCID 86587686HCID 86587686, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

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온도
110 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6cdabc9331554c629165c593af381238
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06777437B2

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