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

HRID 1192240ノート

反応式

HRID 1192240 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-ee90ca04f2c24698bb2e006d8f146ece
出典データセット
uspto-grants-2014_03
特許番号
US08680139B2

反応ノート

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