Acetonitrile → N,N-dimethyl-N'-(5-nitropyridin-2-yl)ethane-1,2-diamine

HRID 1192240

반응식

HRID 1192240 반응식
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.CC(N)C(C)[NH2:14].[CH2:17]([N:19]([CH2:22]C)[CH2:20]C)[CH3:18].C(#N)C>O>[CH3:20][N:19]([CH3:22])[CH2:17][CH2:18][NH:14][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1

참가 물질

6

반응물 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 783082-Chloro-5-nitropyridineHCID 1363622,3-Butanediamine

생성물 1

HCID 3696952N,N-dimethyl-N'-(5-nitropyridin-2-yl)ethane-1,2-diamine수율 42%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a round bottom flask, charged with 2-chloro-5-nitropyridine (1.0 g, 6.3 mmol), dimethylethane-1,2-diamine (0.55 g, 6.3 mmol), triethylamine (0.63 g, 6.3 mmol) and acetonitrile (10 mL). The resulting reaction mixture was stirred at ambient temperature for 9 hours. TLC analysis showed no acid remaining so the mixture was diluted with water and extracted with ethylacetate. The organic layer was separated and washed with brine and water, dried (Na2SO4) and concentrated. The crude material was purified by silica gel chromatography using a 95:5 mixture of dichloromethane and methanol as eluent to afford the title product as a brown solid (0.55 g, 42% yield). 1H NMR (400 MHz, d6-DMSO) δ: 8.91 (1H, m), 8.09 (2H, m), 6.62 (1H, m), 4.10 (1H, m), 3.50 (2H, m), 3.17 (2H, m), 2.21 (6H, s). MS m/z: 211.14 [M+H]+.

후처리

  1. customThe resulting reaction mixture
  2. extractionextracted with ethylacetate
  3. customThe organic layer was separated
  4. washwashed with brine and water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude material was purified by silica gel chromatography
  8. additiona 95:5 mixture of dichloromethane and methanol as eluent

출처 및 근거

ORD 기록
ord-ee90ca04f2c24698bb2e006d8f146ece
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680139B2

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