Sodium Azide → HCID 90410525, compound

HRID 589054Notes

Reaction equation

HRID 589054 reaction equation
N([O-])=O.[Na+].[N+:5]([C:8]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH2:16][C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH2:18])[C:9]=1[NH2:10])([O-:7])=[O:6].C(=O)(O)[O-].[Na+].[N-:30]=[N+:31]=[N-].[Na+]>Cl.O>[N:10]([C:9]1[C:8]([N+:5]([O-:7])=[O:6])=[CH:14][CH:13]=[CH:12][C:11]=1[O:15][CH2:16][C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1)=[CH2:18])=[N+:30]=[N-:31]

Participants

7

Reactant 4

HCID 33557Sodium AzideHCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 90409706HCID 90409706, compound

Product 1

HCID 90410525HCID 90410525, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent3×

Procedure

Sodium nitrite (100 mg, 2 mmol) in water (4 mL, 60 mmol) was added to a solution of 2-nitro-6-[(2-pyridin-2-ylprop-2-en-1-yl)oxy]aniline (350 mg, 1.3 mmol) in 4.0 M hydrogen chloride in water (4 mL, 10 mmol) at 0° C. The reaction was stirred for 5 min and was then neutralized to pH 6-7 with solid sodium bicarbonate. Sodium azide (80 mg, 1 mmol) in water (2 mL) was added drop-wise to the mixture, followed by stirring for 30 min, over which time the reaction mixture became a thick slurry. The resulting mixture was filtered and dried to give 2-{1-[(2-azido-3-nitrophenoxy)methyl]vinyl}pyridine as a dark yellow solid (0.25 g. 83%). LCMS calculated for C14H12N5O3 (M+H)+: m/z=298.1. found: 298.1.

Workup

  1. stirringby stirring for 30 min, over which time the reaction mixture
  2. filtrationThe resulting mixture was filtered
  3. customdried

Sources & evidence

ORD record
ord-5fd4ce53784c4514b2a1f0283161d512
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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