Sodium Azide → HCID 86719518, compound

HRID 1772279Notes

Reaction equation

HRID 1772279 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10]Cl)=[CH:7][C:6]=2[CH:12]=1.[N-:13]=[N+:14]=[N-:15].[Na+]>CN(C)C=O.C(=O)(O)[O-].[Na+]>[N:13]([CH2:10][C:8]1[O:9][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:12][C:6]=2[CH:7]=1)=[N+:14]=[N-:15]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 125644142-Chloromethyl-5-chlorobenzofuran

Product 1

HCID 86719518HCID 86719518, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 5-chloro-2-(chloromethyl)-1-benzofuran (500 mg, 2.49 mmol) in N,N-dimethylformamide (10 ml) was added NaN3 (320 mg, 4.92 mmol) and the contents were stirred overnight at 70° C. The resulting solution was diluted with saturated aqueous sodium bicarbonate (150 ml) and extracted with dichloromethane (3×70 ml). The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified by silica gel column chromatography eluting with petroleum ether to afford 2-(azidomethyl)-5-chloro-1-benzofuran as light brown oil (500 mg, 97%). 1H NMR (300 MHz, CDCl3): δ 7.54 (s, 1H), 7.40 (d, J=9.0 Hz, 1H), 7.25 (d, J=9.0 Hz, 1H), 6.66 (s, 1H), 4.50 (s, 2H).

Workup

  1. extractionextracted with dichloromethane (3×70 ml)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by silica gel column chromatography
  6. washeluting with petroleum ether

Sources & evidence

ORD record
ord-33d0bdf412e04d0188f63b6208c464d1
Source dataset
uspto-grants-2016_02
Patent number
US09249102B2

Reaction notes

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