Sodium Methoxide → 1-(2-fluoro-6-methoxy-4-nitrophenyl)-3-methyl-1H-1,2,4-triazole

HRID 1803174Notes

Reaction equation

HRID 1803174 reaction equation
[CH3:1][O-:2].[Na+].[F:4][C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[C:7](F)[C:6]=1[N:15]1[CH:19]=[N:18][C:17]([CH3:20])=[N:16]1>C1COCC1>[F:4][C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[C:7]([O:2][CH3:1])[C:6]=1[N:15]1[CH:19]=[N:18][C:17]([CH3:20])=[N:16]1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 668602451-(2,6-difluoro-4-nitrophenyl)-3-methyl-1H-1,2,4-triazole

Product 1

HCID 668608961-(2-fluoro-6-methoxy-4-nitrophenyl)-3-methyl-1H-1,2,4-triazoleYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Step S (1): A solution of sodium methanolate (0.5 M in methanol, 17.5 mL, 8.74 mmol) was added to a round bottom flask charged with a solution of 1-(2,6-difluoro-4-nitrophenyl)-3-methyl-1H-1,2,4-triazole (2.1 g, 8.74 mmol, from preparation R, step R(1) in THF (25 mL). A slight pink color resulted. After 2 h, the reaction mixture was concentrated under reduced pressure. The white solid residue was triturated with ˜50 mL of 1 N HCl. The solid was collected by vacuum filtration and dried under high vacuum for several hours to afford 1-(2-fluoro-6-methoxy-4-nitrophenyl)-3-methyl-1H-1,2,4-triazole (1.84 g, 7.15 mmol, 82% yield) as a white solid. LC-MS (M+H)+ 253.1.0. 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 8.22 (s, 1 H), 7.80 (dd, J=9.0, 2.3 Hz, 1 H), 7.76 (t, J=2.0 Hz, 1 H), 3.99 (s, 3 H), 2.52 (s, 3 H).

Workup

  1. customA slight pink color resulted
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customThe white solid residue was triturated with ˜50 mL of 1 N HCl
  4. filtrationThe solid was collected by vacuum filtration
  5. customdried under high vacuum for several hours

Sources & evidence

ORD record
ord-38eeb4da764a498aa5bf518a2a835342
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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