1H-1,2,4-Triazole → HCID 22459731, compound

HRID 2185110Notes

Reaction equation

HRID 2185110 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[O:11][CH3:12].[OH-].[K+].[NH:15]1[CH:19]=[N:18][CH:17]=[N:16]1>CS(C)=O>[CH3:12][O:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[N:15]1[CH:19]=[N:18][CH:17]=[N:16]1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 14797Potassium HydroxideHCID 705192-Chloro-5-nitroanisole

Product 1

HCID 22459731HCID 22459731, compoundYield 18.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

2-Chloro-5-nitroanisole (0.5 g, 2.67 mmol), potassium hydroxide (219 mg, 3.92 mmol) and 1,2,4-triazole (736 mg, 10.66 mmol) were dissolved in dimethyl sulfoxide (2.5 mL), and heated at 110° C. for 24 h. The reaction mixture was poured onto ice-water (100 mL). The solid was collected by filtration and purified by flash column chromatography CH3Cl 2% methanol to yield 110 mg of 3-Methoxy-4-(1H-1,2,4-triazol-1-yl)nitrobenzene. 3-Methoxy-4-(1H-1,2,4-triazol-1-yl)nitrobenzene (105 mg, 0.48 mmol) was dissolved in methanol (10 mL) and 10% palladium on carbon (20 mg) was added. The reaction mixture was hydrogenated at 45 psi overnight. The catalyst was removed by filtration and the solvent evaporated to yield 77 mg of 265A. HPLC method A 97% pure. Mass spectrum M+H+=191.1, 1H 400 MHz NMR (CH3OD): δ8.65 (s, 1H), 8.09 (s, 1H), 7.25 (d, 1H, J=8.56), 6.52 (d, 1H, J=2.19) 6.40-6.35 (m, 1H), 3.83 (s, 3H).

Workup

  1. additionThe reaction mixture was poured onto ice-water (100 mL)
  2. filtrationThe solid was collected by filtration
  3. custompurified by flash column chromatography CH3Cl 2% methanol

Sources & evidence

ORD record
ord-599190e19c7145aab161fd33b820ed5c
Source dataset
uspto-grants-2002_06
Patent number
US06399773B1

Reaction notes

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