Hydrazine, dihydrochloride → HCID 178496107, 화합물

HRID 253250

반응식

HRID 253250 반응식
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:17]([C:20](=O)[CH3:21])[C:18]#[N:19])[CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH2:14][O:15][CH3:16].Cl.Cl.[NH2:25][NH2:26].C(=O)(O)[O-].[Na+]>C(O)C>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:17]2[C:20]([CH3:21])=[N:25][NH:26][C:18]=2[NH2:19])[CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH2:14][O:15][CH3:16]

참가 물질

5

반응물 3

HCID 17548Hydrazine, dihydrochlorideHCID 516892Sodium BicarbonateHCID 668909162-(3,4-Bis{[2-(methyloxy)ethyl]oxy}phenyl)-3-oxobutanenitrile

생성물 1

HCID 178496107HCID 178496107, 화합물수율 74%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of 2-(3,4-bis{[2-(methyloxy)ethyl]oxy}phenyl)-3-oxobutanenitrile (0.57 g, 1.9 mmol) in ethanol (5 mL) was added hydrazine dihydrochloride (0.20 g, 2.2 mmol) The resulting mixture was heated at reflux for 1 hour. It was cooled, pour into a saturated sodium bicarbonate solution (10 mL), and the mixture was extracted with ethyl acetate (3×10 mL). The combined extract was washed with aqueous sodium bicarbonate solution, brine, dried over sodium sulfate, filtered and concentrated to give an oily residue which was purified by flash chromatography (silica gel, 5% methanol-dichloromethane) to provide 4-(3,4-bis{[2-(methyloxy)ethyl]oxy}phenyl)-3-methyl-1H-pyrazol-5-amine (0.46 g, 1.4 mmol, 74% yield). 1H NMR (400 MHz, CDCl3): 6.96-6.92 (m, 2H), 6.87-6.84 (d, d, 1H), 4.19-4.16 (m, 4H), 3.79-3.76 (m, 4H), 3.67 (s, 2H), 3.46 (s, 3H), 3.44 (s, 3H), 2.25 (s, 3H).

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. temperatureIt was cooled
  4. extractionthe mixture was extracted with ethyl acetate (3×10 mL)
  5. extractionThe combined extract
  6. washwas washed with aqueous sodium bicarbonate solution, brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give an oily residue which
  11. customwas purified by flash chromatography (silica gel, 5% methanol-dichloromethane)

출처 및 근거

ORD 기록
ord-6c4ac2695bbe47ee837fa085a8e1b589
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07872014B2

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