Sodium Azide → HCID 60152053, compound

HRID 1689593Notes

Reaction equation

HRID 1689593 reaction equation
[C:1]([C:3]1[C:4](=[C:17]([C:20]#[N:21])[C:18]#[N:19])[O:5][C:6]([CH3:16])([CH3:15])[C:7]=1[C:8]1[CH:13]=[CH:12][C:11](F)=[CH:10][CH:9]=1)#[N:2].[N-:22]=[N+:23]=[N-:24].[Na+]>CS(C)=O>[N:22]([C:11]1[CH:12]=[CH:13][C:8]([C:7]2[C:6]([CH3:16])([CH3:15])[O:5][C:4](=[C:17]([C:20]#[N:21])[C:18]#[N:19])[C:3]=2[C:1]#[N:2])=[CH:9][CH:10]=1)=[N+:23]=[N-:24]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 53415751[3-Cyano-4-(4-fluorophenyl)-5,5-dimethylfuran-2(5H)-ylidene]propanedinitrile

Product 1

HCID 60152053HCID 60152053, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a 200-mL round bottom flask with stirbar was added 2-[3-cyano-4-(4-fluoro-phenyl)-5,5-dimethyl-5H-furan-2-ylidene]-malononitrile (0.20 g, 0.716 mmol) and DMSO (8 mL). The mixture was stirred at room temperature, then sodium azide (0.08 g, 1.23 mmol) was added to it and the reaction continued to react at room temperature. After 2 h, the reaction mixture was completely homogeneous. The product mixture was poured into ice-water (300 mL) and stirred 0.5 h. The yellow precipitate was filtered out through suction filtration. The solid was recrystallized from 1-propanol to give the final product as a yellow solid having a UV spectra as set forth in FIG. 25; (0.19 g, 88% yield). IR (neat): 2924, 2228, 2113, 1567, 1533, 1366, 1279, 1188, 1111, 841 cm−1. 1H NMR (400 MHz, DMSO): δ 7.94 (ddd, J=9.2, 2.8, 2.0 Hz, 2H), 7.40 (ddd, J=9.2, 2.8, 2.0 Hz, 2H), 1.78 (s, 6H); 13C NMR (100 MHz, DMSO): δ 177.1, 176.6, 145.0, 130.6, 123.4, 120.3, 112.3, 111.4, 111.3, 101.6, 100.3, 55.2, 24.9. UV-Vis (CH2Cl2): λmax=384 nm, ε=2.9×104 L·mol−1·cm−1.

Workup

  1. customto react at room temperature
  2. stirringstirred 0.5 h
  3. filtrationThe yellow precipitate was filtered out through suction filtration
  4. customThe solid was recrystallized from 1-propanol

Sources & evidence

ORD record
ord-dc7405b960c64933bbe55ce8c438fae0
Source dataset
uspto-grants-2012_04
Patent number
US08153446B2

Reaction notes

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