1H-1,2,4-Triazole → HCID 18980104, compound

HRID 1924803Notes

Reaction equation

HRID 1924803 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[Br:14][C:15]1[CH:20]=[CH:19][C:18](I)=[CH:17][CH:16]=1.CN[C@H]1CCCC[C@@H]1NC>[Cu]I.CS(C)=O>[Br:14][C:15]1[CH:20]=[CH:19][C:18]([N:1]2[CH:5]=[N:4][CH:3]=[N:2]2)=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 92571H-1,2,4-TriazoleHCID 115221-Bromo-4-iodobenzeneHCID 62657Potassium Phosphate, TribasicHCID 13822957(1S,2S)-(+)-N,N'-Dimethylcyclohexane-1,2-diamine

Product 1

HCID 18980104HCID 18980104, compoundYield 48.9%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 1H-1,2,4-triazole (122 mg, 1.78 mmol, Aldrich), K3PO4 (751 mg, 3.53 mmol, Aldrich), Copper(I) iodide (33.7 mg, 0.177 mmol, Alfa-Aesar), 1-bromo-4-iodobenzene (500 mg, 1.78 mmol, Aldrich), (1S,2S)—N1,N2-dimethylcyclohexane-1,2-diamine (25 mg, 0.18 mmol, Strem) and DMSO (2 mL) was purged with Argon and then heated under microwave condition at 140° C. for 30 min and then at 160° C. for 30 min. The reaction mixture was diluted with H2O and extracted with EtOAc (2×). The organic layers were combined and concentrated in vacuo to a brown oil. The solid was purified by flash chromatography (SiO2, 0-100% EtOAc in hexanes) to yield 195 mg of desired product as a white solid. MS (ESI) 224 (M+H).

Workup

  1. customwas purged with Argon
  2. additionThe reaction mixture was diluted with H2O
  3. extractionextracted with EtOAc (2×)
  4. concentrationconcentrated in vacuo to a brown oil
  5. customThe solid was purified by flash chromatography (SiO2, 0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-9103d7e00ee74c5cb2d890437cf720fa
Source dataset
uspto-grants-2012_05
Patent number
US08178561B2

Reaction notes

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