2-Chlorobenzyl chloride → 2-Chlorobenzyl azide

HRID 1107437Notes

Reaction equation

HRID 1107437 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[Cl:5][C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=1[CH2:8]Cl>CN(C=O)C>[Cl:5][C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=1[CH2:8][N:1]=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 119062-Chlorobenzyl chlorideHCID 33557Sodium Azide

Product 1

HCID 121946022-Chlorobenzyl azide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A cold (0° C.) solution of sodium azide (1.45 g, 22.3 mmol) in 50 ml of DMF was treated with 2-chlorobenzyl chloride (2.4 ml, 18.6 mmol). The reaction mixture was stirred at room temperature for 2 days, under N2 and then partitioned between EtOAc and H2O. The resultant layers were separated and the organic layer was dried over Na2SO4, filtered and then concentrated in vacuo.

Workup

  1. custompartitioned between EtOAc and H2O
  2. customThe resultant layers were separated
  3. dry with materialthe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2303b028f71242c69a7aa8606e2b1239
Source dataset
uspto-grants-2000_05
Patent number
US06060484

Reaction notes

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