Sodium Azide → HCID 72536702, compound

HRID 1618871Notes

Reaction equation

HRID 1618871 reaction equation
N([O-])=O.[Na+].[N:5]1[CH:10]=[CH:9][C:8]([CH:11]=[CH:12][C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1.[N-:20]=[N+:21]=[N-].[Na+].C(=O)(O)[O-].[Na+]>O.Cl>[N:19]([C:16]1[CH:15]=[CH:14][C:13]([CH:12]=[CH:11][C:8]2[CH:9]=[CH:10][N:5]=[CH:6][CH:7]=2)=[CH:18][CH:17]=1)=[N+:20]=[N-:21]

Participants

7

Reactant 4

HCID 33557Sodium AzideHCID 289682HCID 289682, compoundHCID 516892Sodium BicarbonateHCID 23668193Sodium Nitrite

Product 1

HCID 72536702HCID 72536702, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
2.5 °C

Procedure

A solution of sodium nitrite (1.76 g, 25.5 mmol) in 10 mL water was added dropwise to a solution of 4-(2-pyridin-4-yl-vinyl)-phenylamine (2.0 g, 10.2 mmol) in 102 mL 4M HCl at 2-3° C. After stirring the mixture at this temperature for 1 hr, a solution of sodium azide (1.32 g, 20.4 mmol) in 10 mL water was slowly added dropwise, maintaining the temperature at 2-3° C. Stirring was continued for 30 min at this temperature and then the ice bath was allowed to come to ambient temperature while stirring continued overnight Saturated aqueous sodium bicarbonate was added carefully to this mixture with stirring until the evolution of gas subsided. The precipitate was filtered off and dried overnight in the funnel to yield 1.875 g of the product as a beige powder (83% yield), mp 88.2-89.4° C. 1H NMR (400 MHz, CDCl3) δ 8.51 (dd, J=1.4, 6.1 Hz, 2H), 7.46 (ddd, J=1.9, 21, 8.5 Hz, 2H), 7.29 (dd, J=1.4, 6.1 Hz, 2H), 7.18 (d, J=16.4 Hz, 1H), 6.98 (ddd, J=2.0, 2.7, 8.5 Hz, 2H), 8.90 (d, J=16.4 Hz, 1H). 13C NMR (100 MHz, CDCl3) δ 150.3, 144.4, 140.3, 133.1, 132.0, 128.4, 125.7, 120.8, 119.5. λmaxCH3CN 323 nm (ε 3.92×104). IR νmax (cm−1) 2122 (N3).

Workup

  1. stirringStirring
  2. waitwas continued for 30 min at this temperature
  3. customto come to ambient temperature
  4. additionwas added carefully to this mixture
  5. stirringwith stirring until the evolution of gas
  6. filtrationThe precipitate was filtered off
  7. customdried overnight in the funnel

Sources & evidence

ORD record
ord-aacb2051066645169fbf94160a613a55
Source dataset
uspto-grants-2014_07
Patent number
US08772048B2

Reaction notes

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