Water → HCID 86638792, compound

HRID 1618886Notes

Reaction equation

HRID 1618886 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:14]([CH3:16])([CH3:15])[O:13][C:12](=[C:17]([C:20]#[N:21])[C:18]#[N:19])[C:11]=2[C:22]#[N:23])=[CH:6][CH:5]=1)=[N+:2]=[N-:3].[CH2:24]([N:26]([CH2:35][CH3:36])[C:27]1[CH:32]=[CH:31][C:30]([C:33]#[CH:34])=[CH:29][CH:28]=1)[CH3:25].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].O>C(O)C.S([O-])([O-])(=O)=O.[Cu+2]>[C:22]([C:11]1[C:12](=[C:17]([C:20]#[N:21])[C:18]#[N:19])[O:13][C:14]([CH3:15])([CH3:16])[C:10]=1[C:7]1[CH:6]=[CH:5][C:4]([N:1]2[CH:34]=[C:33]([C:30]3[CH:31]=[CH:32][C:27]([N:26]([CH2:35][CH3:36])[CH2:24][CH3:25])=[CH:28][CH:29]=3)[N:3]=[N:2]2)=[CH:9][CH:8]=1)#[N:23]

Participants

7

Reactant 4

HCID 962WaterHCID 114352194'-Diethylaminophenyl acetyleneHCID 23667548Sodium AscorbateHCID 60152053HCID 60152053, compound

Product 1

HCID 86638792HCID 86638792, compound

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 2-[4-(4-azidophenyl)-3-cyano-5,5-dimethyl-5H-furan-2-ylidene]malononitrile (60 mg, 0.20 mmol) and diethyl-(4-ethynyl-phenyl) amine (35 mg, 0.20 mmol) in ethanol (10 mL) was stirred at 60° C. Sodium ascorbate (14 mg, 0.07 mmol in 1 mL water) solution was added followed by copper sulfate (8 mg, 0.03 mmol in 1 mL water) solution. The mixture was stirred at 60° C. for 24 h, cooled, poured into cold water and was stirred at room temperature for 1 h. The precipitate formed was filtered off and air dried. The product was further purified by silica gel column chromatography using hexane/EAC 30-50% and finally recrystallized from dichloromethane/methanol. Yield: 70 mg (73%) Mp: 275° C. IR (neat) 3022, 2230, 1620 cm−1; 1H NMR (400 MHz, CDCl3) 8.09 (s, 1H), 8.05 (d, J=8.8 Hz, 2H), 7.93 (d, J=8.8 Hz, 2H), 7.72 (d, J=8.8 Hz, 2H), 6.73 (d, J=8.8 Hz, 2H), 3.40 (q, 4H), 1.83 (s, 6H), 1.18 (t, 6.8 Hz, 6H); 13CNMR (CDCl3) δ 175.44, 174.40, 149.64, 147.93, 140.30, 129.83, 128.81, 126.91, 126.14, 120.32, 115.77, 114.36, 110.77, 110.79, 109.99, 102.25, 98.91, 59.89, 44.11, 26.07, 12.30. Anal. Calcd for C28H25N7O: C, 70.72; H, 5.30; N, 20.62. Found: C, 69.33; H, 5.63; N, 20.87. UV-Vis(CH2Cl2): λmax=319 nm ε=3.562×104 L.mol−1cm−1.

Workup

  1. stirringThe mixture was stirred at 60° C. for 24 h
  2. temperaturecooled
  3. stirringwas stirred at room temperature for 1 h
  4. customThe precipitate formed
  5. filtrationwas filtered off
  6. customair dried
  7. customThe product was further purified by silica gel column chromatography
  8. customfinally recrystallized from dichloromethane/methanol

Sources & evidence

ORD record
ord-f9efb125e0764635adcb2793b1d7d9e8
Source dataset
uspto-grants-2014_07
Patent number
US08772048B2

Reaction notes

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