Hydrazine, dihydrochloride → HCID 178496107、化合物

HRID 253250

反応式

HRID 253250 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 178496107HCID 178496107、化合物収率 74%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-6c4ac2695bbe47ee837fa085a8e1b589
出典データセット
uspto-grants-2011_01
特許番号
US07872014B2

関連ノート

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