Ammonia → 1-phenyl-1H-1,2,3-triazole-5-carboxamide

HRID 1506624Notes

Reaction equation

HRID 1506624 reaction equation
[C:1]1([N:7]2[C:11]([C:12]([OH:14])=O)=[CH:10][N:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[N:16]1CCOCC1.ClC(OCC(C)C)=O.N.O1CCOCC1>COCCOC>[C:1]1([N:7]2[C:11]([C:12]([NH2:16])=[O:14])=[CH:10][N:9]=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 79724-MethylmorpholineHCID 312751,4-DioxaneHCID 62365Isobutyl chloroformateHCID 28017501-Phenyl-1H-1,2,3-triazole-5-carboxylic acid

Product 1

HCID 184741521-phenyl-1H-1,2,3-triazole-5-carboxamide

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 1-phenyl-1H-1,2,3-triazole-5-carboxylic acid (1.0 g, 5.6 mmol) and 4-methylmorpholine (0.57 g, 5.6 mmol) in 1,2-dimethoxyethane (5 mL), isobutyl chloroformate (0.77, 5.6 mmol) was added to the mixture. After 30 minutes, ammonia in dioxane (16.8 mL, 8.4 mmol) was added to the reaction. Then it was stirred overnight. The solvent was removed and dissolved in 50 mL of ethyl acetate. The organic layer was washed with brine twice. The organic layer was dried with Na2SO4, filtered and concentrated and used without further purification. MS (m/z) 189 [M+H]+.

Workup

  1. customThe solvent was removed
  2. dissolutiondissolved in 50 mL of ethyl acetate
  3. washThe organic layer was washed with brine twice
  4. dry with materialThe organic layer was dried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customused without further purification

Sources & evidence

ORD record
ord-e267bd35a98e4a4aac73c3a79838a321
Source dataset
uspto-grants-2015_12
Patent number
US09220710B2

Reaction notes

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