3,4-Dichlorobenzyl chloride → 4-(Azidomethyl)-1,2-dichlorobenzene

HRID 1709658Notes

Reaction equation

HRID 1709658 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+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH2:5][N:11]=[N+:12]=[N-:13]

Participants

4

Reactant 2

HCID 76093,4-Dichlorobenzyl chlorideHCID 33557Sodium Azide

Product 1

HCID 150652184-(Azidomethyl)-1,2-dichlorobenzene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 3,4-dichlorobenzyl chloride (12.6 g, 64.5 mmol) and sodium azide (7.0 g, 0.11 mole) in absolute ethanol (70 ml) was refluxed for 4.75 hours, cooled and filtered to provide a solution of 3,4-dichlorobenzyl azide. Separately, 2-cyanoacetamide (5.5 g, 65 mmol) was added to a 35° C. solution of sodium (1.5 g, 65 mmol) in absolute ethanol (125 ml), and to the resulting suspension was added the above azide solution dropwise over 10 minutes. The combined mixtures were refluxed for 1 hour, kept 16 hours at ambient temperature and 1 hour at 5° C., and filtered. The crude product was dried under vacuum, dissolved in boiling ethanol (290 ml), filtered hot, and cooled to 0° C. The solid was collected by filtration and dried under vacuum to provide 12.4 g (67%) of 1-(3,4-dichlorobenzyl)-5-amino-1,2,3-triazole-4-carboxamide, m.p 221°-222° C.

Workup

  1. temperaturewas refluxed for 4.75 hours
  2. temperaturecooled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-897a2ce76b224df291c6193ab7a46eea
Source dataset
uspto-grants-1990_08
Patent number
US04950673

Reaction notes

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