Water → HCID 86638790, compound

HRID 1618883Notes

Reaction equation

HRID 1618883 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]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[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]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:15]=2)=[CH:10][CH:9]=1)#[N:2]

Participants

7

Reactant 4

HCID 962WaterHCID 69319AzidobenzeneHCID 23667548Sodium AscorbateHCID 86638786HCID 86638786, compound

Product 1

HCID 86638790HCID 86638790, 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 (150 mg, 0.53 mmol) and azidobenzene (80 mg, 0.67 mmol) in 20 mL ethanol was heated to 50° C. and stirred under N2. Sodium ascorbate (30 mg, 0.15 mmol in 1 mL water) solution was added followed by copper sulfate (20 mg, 0.08 mmol in 2 ml . . . water) solution. The mixture was stirred at 50° C. for 24 h, cooled and 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 silica gel column chromatography using hexane/EAC 30-50% and then recrystallized from dichloromethane/l-propanol. Yield: 140 mg (65%) mp 298° C.; IR (neat) 2930, 2232, 1580 cm−1; 1H NMR (400 MHz, DMSO) δ 9.44 (s, 8.19 (d, J=8.4 Hz, 2H), 7.94-8.00 (m, 2H), 7.63-7.65 (m, 2H), 7.53-7.62 (m, 1H), 1.86 (s, 6H); 13C NMR (CDCl3) δ 177.26, 176.73, 145.69, 136.31, 134.75, 129.74, 129.24, 128.76, 126.64, 125.91, 121.12, 120.02, 112.06, 111.17, 110.98, 102.32, 100.33, 55.58 23.82; Anal, Calcd for C24H16N6O: C, 71.28; H, 3.99; N, 20.78 Found: C, 70.95; H, 3.74; N, 26.04; UV-Vis(CH2Cl2): λmax=384 nm ε=3.22×104 L.mol−1cm−1.

Workup

  1. stirringThe mixture was stirred at 50° 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 crude product was further purified by silica gel column chromatography
  8. customrecrystallized from dichloromethane/l-propanol

Sources & evidence

ORD record
ord-d4a5413976af4c95ac3007009453fa87
Source dataset
uspto-grants-2014_07
Patent number
US08772048B2

Reaction notes

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