Sodium Azide → HCID 60152053, compound

HRID 1618873Notes

Reaction equation

HRID 1618873 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 mind) 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-f20fe6e6604f47c0b9242b1a9a36412d
Source dataset
uspto-grants-2014_07
Patent number
US08772048B2

Reaction notes

Loading…