Dibenzylamine → HCID 68980847, 화합물

HRID 1821807노트

반응식

HRID 1821807 반응식
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([CH3:11])[CH:5]=[CH:4][N:3]=1.[CH2:12]([NH:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.ClCCl.O>[CH2:20]([N:19]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([CH3:11])[CH:5]=[CH:4][N:3]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

참가 물질

7

반응물 3

HCID 7656DibenzylamineHCID 10340Sodium CarbonateHCID 3453632-Chloro-4-methyl-3-nitropyridine

생성물 1

HCID 68980847HCID 68980847, 화합물수율 75%

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of 2-chloro-4-methyl-3-nitropyridine (1.06 g, 6.14 mmol) in tetrahydrofuran (12 mL) under an atmosphere of nitrogen were added dibenzylamine (2.4 mL, 13 mmol) and sodium carbonate (684 mg, 6.45 mmol). The mixture was warmed to reflux for 48 h and cooled to room temperature. The mixture was diluted with dichloromethane (100 mL) and water (100 mL), and the layers were separated. The aqueous layer was extracted with dichloromethane (2×50 mL). The combined organic extracts were washed with 1 N HCl (100 mL) and brine (100 mL), dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by chromatography (silica gel, 10% ethyl acetate/hexanes) to provide 2-(dibenzylamino)-4-methyl-3-nitropyridine (1.53 g, 4.59 mmol, 75%) as a bright yellow oil which solidified upon standing. Rf 0.52 (67:33 hexanes/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ2.32 (3H, s), 4.45 (4H, s), 6.70 (1H, d, J=4.9 Hz), 7.16-7.19 (4H, m), 7.21-7.34 (6H, m), 8.16 (1H, d, J=4.9 Hz); ESI MS m/z 334 [C20H19N3O2+H]+.

후처리

  1. temperatureThe mixture was warmed
  2. temperatureto reflux for 48 h
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with dichloromethane (2×50 mL)
  5. washThe combined organic extracts were washed with 1 N HCl (100 mL) and brine (100 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by chromatography (silica gel, 10% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-0976e21e359749f7ab0a7988e16c585c
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07608627B2

반응 노트

불러오는 중…