Ethanol → ethyl 5-amino-1-benzyl-1H-1,2,3-triazole-4-carboxylate

HRID 1728354Notes

Reaction equation

HRID 1728354 reaction equation
[Na].[C:2]([CH2:4][C:5]([O:7][CH3:8])=[O:6])#[N:3].[CH2:9]([N:16]=[N+:17]=[N-:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH2:19](O)C>>[NH2:3][C:2]1[N:16]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:17]=[N:18][C:4]=1[C:5]([O:7][CH2:8][CH3:19])=[O:6]

Participants

5

Reactant 4

HCID 702EthanolHCID 7747Methyl cyanoacetateHCID 12152Benzyl azideHCID 5360545Sodium

Product 1

HCID 269896ethyl 5-amino-1-benzyl-1H-1,2,3-triazole-4-carboxylateYield 42%

Procedure

To a solution of 1.15 g (0.05 mol) of sodium in 80 mL of absolute ethanol was added 4.5 mL of methyl cyanoacetate and 6.5 g (0.05 mol) of benzyl azide. A white precipitate formed immediately, and the resulting mixture was stirred overnight. The yellowish creamy mixture was poured into 500 mL of ice water, and a crude yellow precipitate was collected by filtration. Recrystallization from ethanol afforded the title compound as a pale yellow solid (5.0 g, 42%). m.p. 153° C.

Workup

  1. customA white precipitate formed immediately
  2. filtrationa crude yellow precipitate was collected by filtration
  3. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-8a7a6f56f98c452f92c5f2d49ef650fe
Source dataset
uspto-grants-1994_07
Patent number
US05326776

Reaction notes

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