Water → HCID 86638791, compound

HRID 1689601Notes

Reaction equation

HRID 1689601 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].[C:24]1([C:30]#[CH:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.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:31]=[C:30]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:3]=[N:2]2)=[CH:9][CH:8]=1)#[N:23]

Participants

7

Reactant 4

HCID 962WaterHCID 10821PhenylacetyleneHCID 23667548Sodium AscorbateHCID 60152053HCID 60152053, compound

Product 1

HCID 86638791HCID 86638791, compound

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-[4-(4-azido phenyl)-3-cyano-5,5-dimethyl-5H-furan-2-ylidene]malononitrile (100 mg, 0.33 mmol) and phenylacetylene (40 mg, 0.40 mmol) in 15 mL ethanol was stirred at 50° C. under N2. Sodium ascorbate (20 mg, 0.10 mmol in 2 mL water) solution was added followed by copper sulfate (12 mg, 0.048 mmol, 2 mL water) solution and stirred at 50° C. for 24 h. The reaction mixture was cooled, poured into cold water (100 mL) and was stirred at room temperature for 1 h. The precipitate formed was filtered off and air-dried. The crude product was further purified by recrystallization from EAC/1-propanol. Yield: 70 mg (52%) mp: 280° C. IR (neat) 3097, 2232, 1645, 1530 cm−1; 1H NMR (400 MHz, DMSO) δ 9.46 (s, 1H), 8.24 (d, J=8.8 Hz, 2H), 8.06 (d, J=8.8 Hz, 1H), 7.95-7.97 (m, 3H), 7.41-7.54 (m, 3H), 1.80 (s, 6H); 13CNMR (DMSO) δ 176.68, 176.52, 149.83, 147.27, 139.40, 130.17, 129.45, 128.86, 128.08, 126.9, 125.20, 120.34, 111.88, 111.00, 110.58, 103.71, 100.49, 54.80, 24.40; Anal. Calcd for C24H16N6O: C, 71.28; H, 3.99; N, 20.78. Found: C, 71.58; H, 3.84; N, 20.64. UV-Vis (CH2Cl2): λmax=369 nm, ε=2.05×104 L·mol−1 cm−1.

Workup

  1. stirringstirred at 50° C. for 24 h
  2. temperatureThe reaction mixture was cooled
  3. stirringwas stirred at room temperature for 1 h
  4. customThe precipitate formed
  5. filtrationwas filtered off
  6. customair-dried
  7. customThe crude product was further purified by recrystallization from EAC/1-propanol

Sources & evidence

ORD record
ord-d40bfd526f824d2ca4af951e57abf5ee
Source dataset
uspto-grants-2012_04
Patent number
US08153446B2

Reaction notes

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