Sodium Azide → HCID 11769343, compound

HRID 1468172Notes

Reaction equation

HRID 1468172 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Br[CH2:6][C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=1)[C:10]([O:12][CH3:13])=[O:11]>CC(N(C)C)=O>[CH3:13][O:12][C:10](=[O:11])[C:9]1[CH:14]=[CH:15][CH:16]=[C:7]([CH2:6][N:1]=[N+:2]=[N-:3])[CH:8]=1

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 517981Methyl 3-(bromomethyl)benzoate

Product 1

HCID 11769343HCID 11769343, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Add sodium azide (0.3 g, 4.8 mmol) to a solution of methyl 3-bromomethylbenzoate (1.00 g, 4.4 mmol) in 10 mL of dimethylacetamide. Stir at room temperature for several h, pour mixture into ice water and extract with EtOAc. Wash combined extracts 4 times with H2O, brine and dry over sodium sulfate. Filter the mixture and concentrate to afford 0.81 g, 97% yield of 3-azidomethyl-benzoic acid methyl ester as an oil.

Workup

  1. extractionextract with EtOAc
  2. washWash
  3. dry with materialdry over sodium sulfate
  4. filtrationFilter the mixture
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-75c3816f7523483e8d0c8ec6c8ae60d9
Source dataset
uspto-grants-2015_04
Patent number
US09000154B2

Reaction notes

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