Sodium Azide → HCID 86688386, compound

HRID 1842577Notes

Reaction equation

HRID 1842577 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Br[CH2:6][C:7]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10]>CN(C=O)C>[N:1]([CH2:6][C:7]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 51358462Methyl 2-(bromomethyl)-5-chlorobenzoate

Product 1

HCID 86688386HCID 86688386, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium azide (158 mg, 2.43 mmol) was added to a solution of methyl 2-(bromomethyl)-5-chlorobenzoate (518 mg, 1.97 mmol) in 3 mL of DMF at room temperature. After stirring overnight, reaction mixture was quenched with 25 mL of water. Aqueous was extracted with ethyl acetate (3×30 mL) and combined organics were washed with water (2×40 mL) and 50 mL of brine. Organics were dried (Na2SO4), filtered, and concentrated under reduced pressure to yield methyl 2-(azidomethyl)-5-chlorobenzoate which was used in the next step without further purification.

Workup

  1. customreaction mixture
  2. customwas quenched with 25 mL of water
  3. extractionAqueous was extracted with ethyl acetate (3×30 mL)
  4. washcombined organics were washed with water (2×40 mL) and 50 mL of brine
  5. dry with materialOrganics were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-903e3385ae234c74aea85c8d60ed6bc2
Source dataset
uspto-grants-2015_02
Patent number
US08946238B2

Reaction notes

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