Dimethyl Sulfoxide → 2-Chlorobenzyl azide

HRID 400815Notes

Reaction equation

HRID 400815 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].CS(C)=O.CCN(C(C)C)C(C)C.[Cl:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25]Cl>O>[N:1]([CH2:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[Cl:18])=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 119062-Chlorobenzyl chlorideHCID 33557Sodium AzideHCID 81531Diisopropylethylamine

Product 1

HCID 121946022-Chlorobenzyl azide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium azide (3.36 g, 51.1 mmol, Eq: 1.05) was charged in the reactor followed by DMSO (35.2 g, 32.0 ml) and Hunig's base (642 mg, 868 μl, 4.87 mmol, Eq: 0.1). The suspension was stirred for 10 Min. at 25° C. Then 1-chloro-2-(chloromethyl)benzene (8 g, 6.29 ml, 48.7 mmol, Eq: 1.00) was added dropwise over 60 min. (Tr=25° C.) and stirred at 25° C. until reaction completion (<2 h). The resulting white suspension was treated with water (1.6 g, 1.6 ml) and stirred for 45 Min. at R.T. The suspension was filtered and the filter cake was washed with DMSO (17.6 g, 16.0 ml) to give a colorless solution of 1-(azidomethyl)-2-chloro-benzene solution.

Workup

  1. customat 25° C
  2. stirringstirred at 25° C. until reaction completion (<2 h)
  3. stirringstirred for 45 Min
  4. customat R.T
  5. filtrationThe suspension was filtered
  6. washthe filter cake was washed with DMSO (17.6 g, 16.0 ml)

Sources & evidence

ORD record
ord-3d6f7de359a64c738b31a2edc9ff0426
Source dataset
uspto-grants-2014_06
Patent number
US08741906B2

Reaction notes

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