Sodium Azide → 4-Azidocoumarin

HRID 19452Notes

Reaction equation

HRID 19452 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][C:4](=[O:12])[CH:3]=1.[N-:13]=[N+:14]=[N-:15].[Na+]>CN(C=O)C>[N:13]([C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][C:4](=[O:12])[CH:3]=1)=[N+:14]=[N-:15]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 873264-chloro-2H-1-benzopyran-2-one

Product 1

HCID 3752284-Azidocoumarin

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-chloro coumarin, (100 mg, 0.54 mmol) was dissolved in 2 mL of DMF at room temperature and followed by the addition of NaN3 (40 mg, 0.62 mmol) and stirring for twelve hours. The reaction mixture was poured onto 10 g of ice, and then stirred for 30 minutes at room temperature. Filtration and drying afforded white powder; yield (80 mg, 80%); mp 159-160° C. 1H-NMR (300 MHz, CDCl3): δ 7.2-7.7 (m, 5H).

Workup

  1. stirringstirred for 30 minutes at room temperature
  2. filtrationFiltration
  3. customdrying
  4. customafforded white powder
  5. customyield (80 mg, 80%)

Sources & evidence

ORD record
ord-3d12bed92d0c4a648cdf840850933612
Source dataset
uspto-grants-2010_06
Patent number
US07745229B2

Reaction notes

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