Water → 5-(3-Bromophenyl)-1H-1,2,4-triazole

HRID 70292

Reaction equation

HRID 70292 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]([C:9](=[NH:12])OC)[CH:6]=[CH:7][CH:8]=1.[CH:13]([NH:15][NH2:16])=O.O>N1C=CC=CC=1>[Br:2][C:3]1[CH:4]=[C:5]([C:9]2[N:12]=[CH:13][NH:15][N:16]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 12229HydrazinecarboxaldehydeHCID 14685566Methyl 3-Bromobenzimidate Hydrochloride

Product 1

HCID 124615465-(3-Bromophenyl)-1H-1,2,4-triazole

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a slurry of methyl 3-bromobenzenecarboximidoate hydrochloride (example IV-21 Step 1; 0.541 g; 2.18 mmol) in pyridine (3 mL) at 0° C. was added a solution of formic hydrazide (0.157 g; 2.62 mmol). The flask was stoppered and gradually warmed to room temperature (overnight) and poured into water (˜20 mL). Precipitated solid was collected by filtration and the filtrate was extracted with EtOAc (×3). Combined extracts were washed (water, brine), dried over Na2SO4, concentrated in vacuo. The residue obtained was combined with the above precipitate, and the whole was purified by flash chromatography (EtOAc/hexanes), affording the title compound as a colorless solid. LC/MS (method A) tR 2.49 min, m/z 224, 226 (M+H, Br isotopes).

Workup

  1. customat 0° C.
  2. customPrecipitated solid
  3. filtrationwas collected by filtration
  4. extractionthe filtrate was extracted with EtOAc (×3)
  5. washCombined extracts were washed (water, brine)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue obtained
  9. customthe whole was purified by flash chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-0b30f80687814be5988667dd12192e9b
Source dataset
uspto-grants-2014_09
Patent number
US08822518B2

Linked notes

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