Water → 4-Azidomethyl-3-chlorobenzonitrile

HRID 1250278Notes

Reaction equation

HRID 1250278 reaction equation
Br[CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[Cl:11].[N-:12]=[N+:13]=[N-:14].[Na+].C(=O)([O-])O.[Na+].O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[N:12]([CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[Cl:11])=[N+:13]=[N-:14]

Participants

7

Reactant 4

HCID 962WaterHCID 33557Sodium AzideHCID 516892Sodium BicarbonateHCID 130420934-(Bromomethyl)-3-chlorobenzonitrile

Product 1

HCID 223499744-Azidomethyl-3-chlorobenzonitrileYield 100%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent

Procedure

A mixture 8.0 g (0.035 mol) of 4-bromomethyl-3-chlorobenzonitrile (J. Pharm. Sci., (1986) 75, 410), 2.7 g (0.042 mol) of sodium azide, 1.2 g (3.4 mmol) of tetrabutylammonium hydrogen sulfate, 0.30 g (3.4 mmol) of sodium hydrogen carbonate, 7 mL of water and 20 mL of toluene was stirred vigorously for 3 days. The phases were separated and the aqueous layer was extracted three times with ether. The combined organic phase was washed with water, dried over sodium sulfate and evaporated to give 6.7 g (100%) of the sub-title compound.

Workup

  1. customThe phases were separated
  2. extractionthe aqueous layer was extracted three times with ether
  3. washThe combined organic phase was washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-86f1f9e530264254831e38a7faa488b4
Source dataset
uspto-grants-2002_01
Patent number
US06337394B2

Reaction notes

Loading…