Hydrochloric Acid → 4-(1H-1,2,4-Triazol-1-yl)benzoic acid

HRID 68783Notes

Reaction equation

HRID 68783 reaction equation
F[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8]CC)=[O:7])=[CH:4][CH:3]=1.[NH:13]1[CH:17]=[N:16][CH:15]=[N:14]1.C([O-])([O-])=O.[K+].[K+].Cl>CN1CCCC1=O>[N:13]1([C:2]2[CH:12]=[CH:11][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=2)[CH:17]=[N:16][CH:15]=[N:14]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 67976Benzoic acid, 4-fluoro-, ethyl ester

Product 1

HCID 7365314-(1H-1,2,4-Triazol-1-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
190 °C

Procedure

To a solution of ethyl 4-fluoro-benzoate (1.68 g) in N-methyl-pyrrolidinone (10 mL) is added 1,2,4-triazole (2.5 g) and K2CO3 (1.5 g) and the mixture is heated at 190° C. in a microwave oven for 30 min. After cooling to room temperature, the mixture is acidified with 2 M aqueous HCl and the precipitate is filtered off, washed with a small amount of water and methanol/dichloromethane and dried by suction to give the acid.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe precipitate is filtered off
  3. washwashed with a small amount of water and methanol/dichloromethane
  4. customdried by suction
  5. customto give the acid

Sources & evidence

ORD record
ord-8f9dd6f9592945aebed360fa170cda28
Source dataset
uspto-grants-2014_09
Patent number
US08822471B2

Reaction notes

Loading…