Sodium Azide → HCID 18476026, compound

HRID 2187622Notes

Reaction equation

HRID 2187622 reaction equation
Br[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9].[N-:21]=[N+:22]=[N-:23].[Na+]>CC(N(C)C)=O>[N:21]([CH2:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])=[N+:22]=[N-:23]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 18476055HCID 18476055, compound

Product 1

HCID 18476026HCID 18476026, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of methyl 5-bromomethyl-2-(4-fluorobenzyl)benzoate (3.8 g), sodium azide (2.9 g) and dimethyl acetamide (50 ml) was stirred under an inert atmosphere for 16 hours. The dimethyl acetamide was evaporated and the residue was partitioned between water and ethyl acetate. The organic layer was separated, dried, evaporated to dryness and purified by flash chromatography using iso-hexane/ethyl acetate (80:20) as eluant to give methyl 5-azidomethyl-2-(4-fluorobenzyl)benzoate (3.23 g) as a colourless gum.

Workup

  1. customThe dimethyl acetamide was evaporated
  2. customthe residue was partitioned between water and ethyl acetate
  3. customThe organic layer was separated
  4. customdried
  5. customevaporated to dryness
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-ae542cdab1a543e5b625d617936a7ef6
Source dataset
uspto-grants-2002_06
Patent number
US06410539B1

Reaction notes

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