2-(Azidomethyl)-1,3-difluorobenzene → 1-(2,6-difluorobenzyl)-5-methyl-1H-1,2,3-triazole-4-carboxamide

HRID 414101Notes

Reaction equation

HRID 414101 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[C:3]=1[CH2:4][N:5]=[N+:6]=[N-:7].[CH2:13]([C:17]([NH2:19])=[O:18])[C:14]#[C:15]C>O1CCOCC1>[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[C:3]=1[CH2:4][N:5]1[C:14]([CH3:15])=[C:13]([C:17]([NH2:19])=[O:18])[N:7]=[N:6]1

Participants

4

Reactant 2

HCID 108883232-(Azidomethyl)-1,3-difluorobenzeneHCID 21282587But-2-ynecarboxamide

Product 1

HCID 212826291-(2,6-difluorobenzyl)-5-methyl-1H-1,2,3-triazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

16.9 g (0.1 mole) of 2,6-difluorobenzyl azide and 8.3 g (0.1 mole) of but-2-ynecarboxamide are heated in 20 ml of dioxane for 16 hours to 100° C. After removing the dioxane by evaporation, the desired isomer is separated by column chromatography, to give 1-(2,6-difluorobenzyl)-5-methyl-1H-1,2,3-triazole-4-carboxamide with a melting point of 208°-210° C. (recrystallisation from methanol).

Workup

  1. customAfter removing the dioxane
  2. customby evaporation
  3. customthe desired isomer is separated by column chromatography

Sources & evidence

ORD record
ord-041fba32ce2c4336856fe3d1dd668d44
Source dataset
uspto-grants-1988_12
Patent number
US04789680

Reaction notes

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