Cyanoacetamide → HCID 339321, compound

HRID 2046994Notes

Reaction equation

HRID 2046994 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)=[N+:2]=[N-:3].[C:13]([CH2:15][C:16]([NH2:18])=[O:17])#[N:14]>[O-]CC.[Na+]>[NH2:14][C:13]1[N:1]([CH2:4][C:5]2[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=2)[N:2]=[N:3][C:15]=1[C:16]([NH2:18])=[O:17]

Participants

4

Reactant 2

HCID 7898CyanoacetamideHCID 109317671-(Azidomethyl)-4-methoxybenzene

Product 1

HCID 339321HCID 339321, compound

Reagents, catalysts & solvents 1

HCID 2723922Sodium ethoxideSolvent

Procedure

A mixture of 1-(azidomethyl)-4-methoxybenzene (5 g) and 2-cyanoacetamide (5 g) was added to a solution of sodium ethoxide (made from 1.6 g of sodium in 100 mL of ethanol). The resulting mixture was refluxed for 20 h. It was cooled down to room temperature and solvent was removed under reduced pressure. The remaining solid was dissolved in water (20 mL) and extracted with ethyl acetate (3×50 mL). The extracts were combined, washed with brine and dried over sodium sulfate. Solvent was removed and the residue was crystallized from hot water to give the desired product 5-amino-1-(4-methoxybenzyl)-1H-1,2,3-triazole-4-carboxamide. ESMS calculated for C11H13N5O2 (m/z): 247.1; found (M+H+): 248.1

Workup

  1. temperatureThe resulting mixture was refluxed for 20 h
  2. customsolvent was removed under reduced pressure
  3. dissolutionThe remaining solid was dissolved in water (20 mL)
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. customSolvent was removed
  8. customthe residue was crystallized from hot water

Sources & evidence

ORD record
ord-1bbda22c08bb4ba4ada0ca1bec09cb5f
Source dataset
uspto-grants-2013_11
Patent number
US08592432B2

Reaction notes

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