Sodium Azide → HCID 86597516, compound

HRID 2063234Notes

Reaction equation

HRID 2063234 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[C:5]([CH:12]([NH2:16])[CH2:13][CH2:14]Br)([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].C1(C)C=CC=CC=1>[C:5]([CH:12]([NH2:16])[CH2:13][CH2:14][N:1]=[N+:2]=[N-:3])([O:7][C:8]([CH3:10])([CH3:11])[CH3:9])=[O:6]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 14193053HCID 14193053, compound

Product 1

HCID 86597516HCID 86597516, compoundYield 85.1%

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 1140TolueneSolvent

Procedure

An aqueous solution (5 mL) of NaN3 (1.4 g; 21.5 mmol) and 2-3 drops of Aliquat 336 are added to a stirred solution of 3-BOC-amino-propyl bromide (5 g; 21.5 mmol) in toluene (10 mL); the mixture is heated at the reflux temperature for 4 hrs. After cooling at r.t., the organic phase is separated, dried over Na2SO4, and evaporated to dryness in vacuum to give 3-BOC-amino-propyl azide (3.75 g; 18.3 mmol) as a transparent oil (yield 85%).

Workup

  1. temperaturethe mixture is heated at the reflux temperature for 4 hrs
  2. customthe organic phase is separated
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness in vacuum

Sources & evidence

ORD record
ord-0e0a637064014624b6b90ccccbf9089e
Source dataset
uspto-grants-2012_10
Patent number
US08288368B2

Reaction notes

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