Sodium Azide → HCID 86688386, compound

HRID 874182Notes

Reaction equation

HRID 874182 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, compoundYield 97%

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. The aqueous was extracted with ethyl acetate (3×30 mL) and the combined organics were washed with water (2×40 mL) and 50 mL of brine. The organics were dried (Na2SO4), filtered, and concentrated under reduced pressure to yield methyl 2-(azidomethyl)-5-chlorobenzoate (429 mg, 97%) as an off-white solid, which was used in the next step without further purification.

Workup

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

Sources & evidence

ORD record
ord-eef367bc7e654134a7635417224f8dd4
Source dataset
uspto-grants-2015_03
Patent number
US08980878B2

Reaction notes

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