Ethyl bromoacetate → Ethyl 1H-1,2,4-triazole-1-acetate

HRID 64064Notes

Reaction equation

HRID 64064 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15]>CN(C=O)C>[N:1]1([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:5]=[N:4][CH:3]=[N:2]1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 92571H-1,2,4-TriazoleHCID 11430Potassium Carbonate

Product 1

HCID 557521Ethyl 1H-1,2,4-triazole-1-acetateYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1H-1,2,4-triazol (2 g, 29.9 mmol, 1.0 eq) in DMF were added K2CO3 (12.3 g, 88.9 mmol, 3 eq.) and ethyl 2-bromoacetate (4.8 g, 29.9 mmol, 1 eq). The mixture was stirred at RT for 16 h. The mixture was quenched and extracted as in Intermediate Example 5(a). The solvent was distilled off to give the product in 65% yield (3 g). LC-MS (ESI): Calculated mass: 155.0; Observed mass: 156.1 [M+H]+ (rt: 0.113 min).

Workup

  1. customThe mixture was quenched
  2. extractionextracted as in Intermediate Example 5(a)
  3. distillationThe solvent was distilled off
  4. customto give the product in 65% yield (3 g)
  5. custom156.1 [M+H]+ (rt: 0.113 min)

Sources & evidence

ORD record
ord-509fe4691649464e92776e45b5ffda9f
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

Loading…