Potassium Carbonate → HCID 10732468, compound

HRID 1488499Notes

Reaction equation

HRID 1488499 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][N:10]2[CH:14]=[N:13][N:12]=[CH:11]2)=[CH:5][CH:4]=1)#[N:2].[F:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Br)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([N:9]([N:10]2[CH:11]=[N:12][N:13]=[CH:14]2)[CH2:20][C:19]2[CH:22]=[CH:23][C:16]([F:15])=[CH:17][CH:18]=2)=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 10307909Benzonitrile, 4-(4H-1,2,4-triazol-4-ylamino)-

Product 1

HCID 10732468HCID 10732468, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

40 Milliliters of acetonitrile was added to 500 mg of 4-[(4-cyanophenyl)amino]-4H-1,2,4-triazole, 0.42 ml of 4-fluorobenzyl bromide and 746 mg of potassium carbonate and the mixture was stirred for 2 hours at room temperature. The solvent was removed by distillation under reduced pressure, and water was added to the resulting residue, which was then extracted with chloroform. The chloroform layer was dried over anhydrous magnesium sulfate and the solvent was removed by distillation. The residue was subjected to silica gel column chromatography to give crude crystals from the chloroform/methanol (100/2) eluate. The crude crystals were recrystallized from ethyl acetate to give 314 mg of 4-[N-(4-cyanophenyl)-N-(4-fluorobenzyl)amino]-4H-1,2,4-triazole.

Workup

  1. customThe solvent was removed by distillation under reduced pressure, and water
  2. additionwas added to the resulting residue, which
  3. extractionwas then extracted with chloroform
  4. dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was removed by distillation
  6. customto give crude crystals from the chloroform/methanol (100/2) eluate
  7. customThe crude crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-cfab5a7575f744baad3dcd3d2f9b8bd1
Source dataset
uspto-grants-1997_10
Patent number
US05674886

Reaction notes

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