Sodium Azide → HCID 11769343, compound

HRID 1242023Notes

Reaction equation

HRID 1242023 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].[N-:13]=[N+:14]=[N-:15].[Na+]>CN(C=O)C.C(Cl)(Cl)Cl>[N:13]([CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])=[N+:14]=[N-:15]

Participants

5

Reactant 2

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

Product 1

HCID 11769343HCID 11769343, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 3-(bromomethyl)benzoate (1.0 g, 4.4 mmol) in anhydrous DMF (10 mL) was added sodium azide (285 mg, 4.4 mmol). The resulting mixture was heated at 50° C. for 2 h, cooled, diluted with CHCl3 (100 mL), washed with water (5×50 mL), dried over MgSO4 and concentrated under reduced pressure to yield methyl 3-(azidomethyl)benzoate (0.84 g, quant.), which was used without purification. 1H-NMR (CDCl3): δ 8.01 (2H, m), 7.44–7.54 (2H, m), 4.42 (2H, s), 3.94 (3H, s).

Workup

  1. temperaturecooled
  2. washwashed with water (5×50 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ea4bec9ce9824341a294614f175ad7f4
Source dataset
uspto-grants-2006_10
Patent number
US07115640B2

Reaction notes

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