Water → Ethyl 5-amino-1-phenyl-1H-1,2,3-triazole-4-carboxylate

HRID 1693567Notes

Reaction equation

HRID 1693567 reaction equation
CC[O-].[Na+].[C:5]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])#[N:6].[N:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[N+:14]=[N-:15].O>CCO>[CH2:11]([O:10][C:8]([C:7]1[N:15]=[N:14][N:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:5]=1[NH2:6])=[O:9])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 7764Ethyl cyanoacetateHCID 69319AzidobenzeneHCID 2723922Sodium ethoxide

Product 1

HCID 253349Ethyl 5-amino-1-phenyl-1H-1,2,3-triazole-4-carboxylateYield 51%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a freshly prepared NaOEt (1.18 mmol) solution in EtOH (0.75 mL) is added ethyl cyanoacetate (100 mg, 0.88 mmol) at 0° C. After stirring at 0° C. for 10 min., azido-benzene (100 mg, 0.84 mmol, prepared according to the method reported by M. Kurumi et al. Heterocycles. 2000, 53, 2809) is added. After the addition, the mixture is allowed to slowly warm up to room temperature and stirred for 14 h. The mixture is then treated with water (3 mL) and extracted with EtOAc (3×3 mL). The combined extracts is concentrated and purified by flash column chromatography (silica gel, 0%-70% EtOAc/hexane) to provide 5-amino-1-phenyl-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester as a white solid (100 mg, 51%). HPLC-MS calculated C11H12N4O2 (M+1+): 233.1. Found: 233.1.

Workup

  1. addition2000, 53, 2809) is added
  2. additionAfter the addition
  3. temperatureto slowly warm up to room temperature
  4. stirringstirred for 14 h
  5. extractionextracted with EtOAc (3×3 mL)
  6. concentrationThe combined extracts is concentrated
  7. custompurified by flash column chromatography (silica gel, 0%-70% EtOAc/hexane)

Sources & evidence

ORD record
ord-fbc9e9fd187b45048606f58850066015
Source dataset
uspto-grants-2012_04
Patent number
US08158634B2

Reaction notes

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