Water → HCID 86638789, 화합물

HRID 1689599노트

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HRID 1689599 반응식
[C:1]([C:3]1[C:4](=[C:18]([C:21]#[N:22])[C:19]#[N:20])[O:5][C:6]([CH3:17])([CH3:16])[C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]#[CH:15])=[CH:10][CH:9]=1)#[N:2].[N:23]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[N+:24]=[N-:25].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].O>C(O)C.S([O-])([O-])(=O)=O.[Cu+2]>[C:1]([C:3]1[C:4](=[C:18]([C:19]#[N:20])[C:21]#[N:22])[O:5][C:6]([CH3:17])([CH3:16])[C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:25]=[N:24][N:23]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH:15]=2)=[CH:10][CH:9]=1)#[N:2]

참가 물질

7

반응물 4

HCID 962WaterHCID 1390231-AzidooctaneHCID 23667548Sodium AscorbateHCID 86638786HCID 86638786, 화합물

생성물 1

HCID 86638789HCID 86638789, 화합물

시약·촉매·용매 2

HCID 24462Copper Sulfate촉매HCID 702Ethanol용매

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온도
50 °C

실험 절차

A mixture of 2-[3-cyano-4-(4-ethynyl-phenyl)-5,5-dimethyl-5H-furan-2-ylidene]malononitrile (90 mg, 0.34 mmol) and 1-azidooctane (80 mg, 0.51 mmol) in 15 mL ethanol was stirred at 50° C. under nitrogen and a solution of sodium ascorbate (25 mg, 0.12 mmol in 1 mL water) was added, followed by copper sulfate (15 mg, 0.06 mmol in 1 mL water) solution. The resulting mixture was stirred at the same temperature for 24 h, cooled and the reaction mixture was poured into cold water (100 mL). The mixture was stirred overnight at room temperature, the precipitate formed was filtered off and air dried. The crude product was recrystallized from dichloromethane/1-propanol. Yield: 70 mg (46%) Mp (DSc): 203° C.; IR (neat) 2933, 2974, 2266, 1574, 1565 cm−1; 1H NMR (400 MHz, CDCl3) δ 8.02 (d, J=8.4 Hz 2H), 7.87 (s, 1H), 7.85 (d, J=8.4 Hz, 2H), 4.39 (t, J=7.2 Hz, 2H), 1.94-1.96 (m, 2H), 1.82 (s, 6H), 1.20-1.31 (m, 10H), 0.82 (t, 3H); 13C NMR (CDCl3) δ 176.69, 175.14, 145.30, 136.33, 129.01, 126.40, 125.91, 121.03, 111.20, 110.47, 110.38, 100.79, 99.08, 59.85, 50.44, 31.41, 30.01, 29.41, 28.76, 28.66, 26.20, 22.31, 13.78; Anal. Calcd for C26H28N6O: C, 70.89; H, 6.41, N 19.08. Found: C, 70.59, H, 6.18; N, 19.37. UV-Vis (CH2Cl2): λmax=384 nm ε=3.01×104 L·mol−1 cm−1.

후처리

  1. stirringThe resulting mixture was stirred at the same temperature for 24 h
  2. temperaturecooled
  3. stirringThe mixture was stirred overnight at room temperature
  4. customthe precipitate formed
  5. filtrationwas filtered off
  6. customair dried
  7. customThe crude product was recrystallized from dichloromethane/1-propanol
  8. custom203° C.

출처 및 근거

ORD 기록
ord-44939f5eeb2a477eb04ac8ae98f52526
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153446B2

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