Sodium Azide → HCID 60152053, compound

HRID 1618879Notes

Reaction equation

HRID 1618879 reaction equation
N([O-])=O.[Na+].[NH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:16]([CH3:18])([CH3:17])[O:15][C:14](=[C:19]([C:22]#[N:23])[C:20]#[N:21])[C:13]=2[C:24]#[N:25])=[CH:8][CH:7]=1.[N-:26]=[N+:27]=[N-].[Na+]>O.Cl>[N:5]([C:6]1[CH:7]=[CH:8][C:9]([C:12]2[C:16]([CH3:17])([CH3:18])[O:15][C:14](=[C:19]([C:22]#[N:23])[C:20]#[N:21])[C:13]=2[C:24]#[N:25])=[CH:10][CH:11]=1)=[N+:26]=[N-:27]

Participants

6

Reactant 3

HCID 33557Sodium AzideHCID 23668193Sodium NitriteHCID 86638788HCID 86638788, compound

Product 1

HCID 60152053HCID 60152053, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

A solution of NaNO2 (0.69 g, 10.0 mmol) in 10 mL water was added dropwise to a solution of 2-[4-(4-aminophenyl)-3-cyano-5,5-dimethyl-5H-furan-2-ylidene] malononitrile (1.4 g, 5.0 mmol) in 30 mL 4M HCl at 0-5° C. After stirring the mixture at this temperature for 46 min, a solution of NaN3 (0.53 g, 8.0 mmol) in 10 mL water was added dropwise to the mixture at the same temperature. Stirring was continued for 1 h below 5° C. and then at room temperature overnight. The precipitate formed was filtered off, washed with water and air-dried. The yellow product was recrystallized from dichloromethane/1-propanol. Yield: 1.25 g (82%). Mp; 184° C. IR (neat) 3056, 2990, 2235, 2122, 2091, 1601, 1568 cm−1; 1H NMR (400 MHz, DMSO) δ 7.90 (d, J=8.8 Hz, 2H), 7.26 (d, J=8.8 Hz, 2H), 1.86 (s, 6H); 13C NMR (100 MHz, CDCl3) δ 177.1, 176.6, 145.0, 130.61, 123.4, 120.30, 112.35, 111.4, 111.3, 101.60, 100.30, 55.20, 24.90; Anal, Calcd for C16H10N6O: C, 63.57; H, 3.33; N, 27.80. Found: C, 63.51H, 3.44; N, 27.20; UV-Vis (CH2Cl2): λmax=384 nm ε=2.9×104 L.mol−1cm−1.

Workup

  1. stirringStirring
  2. waitwas continued for 1 h below 5° C.
  3. customat room temperature
  4. customovernight
  5. customThe precipitate formed
  6. filtrationwas filtered off
  7. washwashed with water
  8. customair-dried
  9. customThe yellow product was recrystallized from dichloromethane/1-propanol

Sources & evidence

ORD record
ord-9b0dc5b5a67a4ad8b7eaab2baac7ac5b
Source dataset
uspto-grants-2014_07
Patent number
US08772048B2

Reaction notes

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