2-Iodobenzoic acid → 2-(2H-1,2,3-Triazol-2-yl)benzoic acid

HRID 2382579Notes

Reaction equation

HRID 2382579 reaction equation
I[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[NH:11]1[CH:15]=[CH:14][N:13]=[N:12]1.CN[C@@H]1CCCC[C@H]1NC>CN(C=O)C.CCOC(C)=O.[Cu]I>[N:11]1[N:12]([C:2]2[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])[N:13]=[CH:14][CH:15]=1

Participants

7

Reactant 3

HCID 69412-Iodobenzoic acidHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 178418936HCID 178418936, compound

Product 1

HCID 213135922-(2H-1,2,3-Triazol-2-yl)benzoic acid

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 2-iodobenzoic acid (3.0 g, 12.09 mmol) in DMF was treated with (1.5 g, 21.7 mmol) 1,2,3-triazole, 7.08 g (21.7 mmol) CsCO3, 114 mg (0.60 mmol) CuI and 310 mg (2.17 mmol) trans-N,N′-dimethylcyclohexane-1,2-diamine. The mixture was heated at 120° C. for 10 min in a microwave reactor. The reaction was cooled to rt, diluted with EtOAc, and filtered through Celite. The residue was purified by gradient elution on SiO2 (0 to 10% MeOH in DCM with 0.1% AcOH) to give the faster eluting desired 2-(2H-1,2,3-triazol-2-yl)benzoyl acid, B-1. Data for B-1: 1HNMR (500 MHz, DMSO-d6) δ 13.05 (br s, 1H), 8.12 (s, 2H), 7.81-7.52 (m, 4H) ppm. The undesired 2-(1H-1,2,3-triazol-2-yl)benzoic acid (B-2) eluted second.

Workup

  1. temperatureThe reaction was cooled to rt
  2. filtrationfiltered through Celite
  3. customThe residue was purified by gradient elution on SiO2 (0 to 10% MeOH in DCM with 0.1% AcOH)
  4. customto give the
  5. washfaster eluting desired 2-(2H-1,2,3-triazol-2-yl)benzoyl acid
  6. washThe undesired 2-(1H-1,2,3-triazol-2-yl)benzoic acid (B-2) eluted second

Sources & evidence

ORD record
ord-df79b8f20af74d3c937be0070053b970
Source dataset
uspto-grants-2012_09
Patent number
US08263586B2

Reaction notes

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