Water → 4-(Azidomethyl)-1,2-dichlorobenzene

HRID 2170528Notes

Reaction equation

HRID 2170528 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH2:5]Cl.[N-:11]=[N+:12]=[N-:13].[Na+].O>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:5][N:11]=[N+:12]=[N-:13])[CH:7]=[CH:8][C:9]=1[Cl:10]

Participants

5

Reactant 3

HCID 962WaterHCID 76093,4-Dichlorobenzyl chlorideHCID 33557Sodium Azide

Product 1

HCID 150652184-(Azidomethyl)-1,2-dichlorobenzeneYield 138.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 3,4-dichlorobenzyl chloride (10 g, 0.05 mol), sodium azide (5 g, 0.08 mol) in DMSO (100 mL) was stirred at room temperature overnight. The mixture was poured into water (150 mL). The water layer was extracted with ethyl acetate (100 ml×3). The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by distillation to give the title compound as an oil (14 g, quantitative yield). LC/MS: m/z 203 (M+H)+, Rt: 2.26 min.

Workup

  1. extractionThe water layer was extracted with ethyl acetate (100 ml×3)
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. distillationThe residue was purified by distillation

Sources & evidence

ORD record
ord-9cb0639877eb4a08aa35c24fb64a4c96
Source dataset
uspto-grants-2015_06
Patent number
US09051281B2

Reaction notes

Loading…