Sodium Azide → 3-Azidocoumarin

HRID 19451Notes

Reaction equation

HRID 19451 reaction equation
[NH2:1][C:2]1[C:3](=[O:12])[O:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.N([O-])=O.[Na+].[N-:17]=[N+:18]=[N-].[Na+]>Cl>[N:1]([C:2]1[C:3](=[O:12])[O:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)=[N+:17]=[N-:18]

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 742173-AminocoumarinHCID 23668193Sodium Nitrite

Product 1

HCID 532385033-Azidocoumarin

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
2.5 °C

Procedure

3-Aminocoumarin (250 mg, 1.6 mmol) was dissolved in 30 mL of 3% HCl at room temperature. After cooling to 0-5° C., the solution was added drop-wise to a solution of NaNO2 (160 mg, 2.3 mmol) and stirred for two hours. Upon addition of NaN3 (150 mg, 2.3 mmol), the mixture was stirred at 0-5° C. for two hours followed by stirring at room temperature for three and a half hours. The precipitate was filtered, washed to neutral pH with water and dried under vacuum to afford a white solid; yield (226 mg, 78%); mp: 108-112° C.; 1H-NMR (300 MHz, CDCl3): δ 7.2-7.6 (m, 5H).

Workup

  1. stirringthe mixture was stirred at 0-5° C. for two hours
  2. stirringby stirring at room temperature for three and a half hours
  3. filtrationThe precipitate was filtered
  4. washwashed to neutral pH with water
  5. customdried under vacuum
  6. customto afford a white solid
  7. customyield (226 mg, 78%)

Sources & evidence

ORD record
ord-a1b41d40808d4c6bb7a8bc994e145af5
Source dataset
uspto-grants-2010_06
Patent number
US07745229B2

Reaction notes

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