Hydrochloric Acid → HCID 86720529, compound

HRID 1755227Notes

Reaction equation

HRID 1755227 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[N:11][C:10]([C:13]([O:15]C)=[O:14])=[N:9]2)=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO.C1COCC1>[I:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[N:11][C:10]([C:13]([OH:15])=[O:14])=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 86720530HCID 86720530, compound

Product 1

HCID 86720529HCID 86720529, compoundYield 86.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

Methyl 1-(4-iodophenyl)-1,2,4-triazole-3-carboxylate (830 mg, 2.5 mmol) was dissolved in MeOH (20 mL) and THF (10 mL). 1 M NaOH (2.5 mL, 2.5 mmol) was added and the mixture stirred at room temperature for 2 h. Additional 1 M NaOH was added (2.5 mL, 2.5 mmol) and the reaction was heated to 50° C. for 30 minutes. After cooling to room temperature, the pH was adjusted to 4 by the addition of 6 M HCl, MeOH and THF were removed under reduced pressure and the resulting white precipitate was collected by filtration and dried in vacuo to obtain 680 mg (86% yield) of 1-(4-iodophenyl)-1,2,4-triazole-3-carboxylic acid.

Workup

  1. temperaturethe reaction was heated to 50° C. for 30 minutes
  2. temperatureAfter cooling to room temperature
  3. customwere removed under reduced pressure
  4. filtrationthe resulting white precipitate was collected by filtration
  5. customdried in vacuo

Sources & evidence

ORD record
ord-035145c02dfa4160ab35fbaade5d57e0
Source dataset
uspto-grants-2015_10
Patent number
US09169261B2

Reaction notes

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