Water → HCID 86638789, compound

HRID 1689599Notes

Reaction equation

HRID 1689599 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

HCID 86638789HCID 86638789, compound

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

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.

Workup

  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.

Sources & evidence

ORD record
ord-44939f5eeb2a477eb04ac8ae98f52526
Source dataset
uspto-grants-2012_04
Patent number
US08153446B2

Reaction notes

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