Triethylamine → HCID 178496121, 화합물

HRID 253243

반응식

HRID 253243 반응식
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:11]([O:12][CH2:13][CH2:14][O:15][CH3:16])=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:17][C:18]#[N:19].[H-].[Na+].C(OCC)(=O)C.Cl.Cl.[NH2:30]N.[CH2:32]([N:34](CC)CC)[CH3:33].C(=O)(O)[O-].[Na+]>C1COCC1.C(O)C.O>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:11]([O:12][CH2:13][CH2:14][O:15][CH3:16])=[CH:10][CH:9]=[CH:8][C:7]=1[C:17]1[C:32]([CH3:33])=[N:34][NH:19][C:18]=1[NH2:30]

참가 물질

10

반응물 6

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 17548Hydrazine, dihydrochlorideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 66889543(2,3-Bis{[2-(methyloxy)ethyl]oxy}phenyl)acetonitrile

생성물 1

HCID 178496121HCID 178496121, 화합물수율 120%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

To a solution of (2,3-bis{[2-(methyloxy)ethyl]oxy}phenyl)acetonitrile (0.93 g, 3.52 mmol) in THF (20 mL) was added sodium hydride (0.42 g, 10.56 mmol) and ethyl acetate (1.55 g, 17.60 mmol), and the mixture was stirred at 60° C. for 90 min. After cooling to 0° C., water was added (50 mL), the aqueous layer was washed with dichloro-methane (3×25 mL), acidified with 1N HCl to pH 3, and extracted with ethyl acetate (3×50 mL). The ethyl acetate layer was washed with brine (50 mL), dried with sodium sulfate, and concentrated to give a yellow oil. This oil was dissolved in dry ethanol (5 mL), and hydrazine dihydrochloride (0.44 g, 4.20 mmol) and triethylamine (0.22 g, 2.10 mmol) were added. The reaction mixture was refluxed for 90 min, cooled to rt, and added into sat. sodium bicarbonate (100 mL). The aqueous layer was extracted with dichloromethane (3×50 mL), the organic layer was dried with sodium sulfate, and concentrated. Column chromatography on silica (95:5 dichloromethane/methanol) afforded 4-(2,3-bis{[2-(methyloxy)ethyl]oxy}phenyl)-3-methyl-1H-pyrazol-5-amine (0.81 g, 71% yield) as a pale yellow oil. 1H NMR (400 MHz, d4-methanol) δ7.08 (t, 1H), 6.97 (dd, 1H), 6.85 (dd, 1H), 4.18 (m, 2H), 3.90 (m, 2H), 3.78 (m, 2H), 3.47 (m, 2H), 3.43 (s, 3H), 3.23 (s, 3H), 2.19 (s, 3H).

후처리

  1. temperatureAfter cooling to 0° C.
  2. washthe aqueous layer was washed with dichloro-methane (3×25 mL)
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. washThe ethyl acetate layer was washed with brine (50 mL)
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated
  7. customto give a yellow oil
  8. temperatureThe reaction mixture was refluxed for 90 min
  9. temperaturecooled to rt
  10. extractionThe aqueous layer was extracted with dichloromethane (3×50 mL)
  11. dry with materialthe organic layer was dried with sodium sulfate
  12. concentrationconcentrated

출처 및 근거

ORD 기록
ord-3d42db3ab05145c4b40cca4f457b2111
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07872014B2

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