Sodium Azide → Methyl 4-(azidomethyl)-1-naphthoate

HRID 735894Notes

Reaction equation

HRID 735894 reaction equation
Br[CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]([O:15][CH3:16])=[O:14])=[CH:5][CH:4]=1.[N-:17]=[N+:18]=[N-:19].[Na+]>CS(C)=O.O>[N:17]([CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]([O:15][CH3:16])=[O:14])=[CH:5][CH:4]=1)=[N+:18]=[N-:19]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 103338131-Naphthalenecarboxylic acid, 4-(bromomethyl)-, methyl ester

Product 1

HCID 20763045Methyl 4-(azidomethyl)-1-naphthoateYield 77%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 4-(bromomethyl)-1-naphthoate (30 g, 0.107 mol) in anhydrous DMSO (300 mL) was added NaN3 portion wise (14 g, 0.215 mol) at 0° C. and stirred at rt for 16 h. Then the reaction mixture was diluted with water (500 mL), extracted with EtOAc (2×250 mL), washed with water, brine and dried over MgSO4. The solvent was removed under vacuum to give methyl 4-(azidomethyl)-1-naphthoate (20 g, 77%).

Workup

  1. extractionextracted with EtOAc (2×250 mL)
  2. washwashed with water, brine
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-1603d0d10eef4ff58108e96f77f08116
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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