Hydroxylamine → HCID 178434783, compound

HRID 2097623Notes

Reaction equation

HRID 2097623 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]([C:12]2[C:16]([CH3:17])=[N:15][O:14][N:13]=2)=O)[CH:6]=[CH:7][CH:8]=1)#[N:2].P(Cl)(Cl)(Cl)(Cl)Cl.[NH2:24][OH:25]>C1C=CC=CC=1>[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]([C:12]2[C:16]([CH3:17])=[N:15][O:14][N:13]=2)=[N:24][OH:25])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 24819Phosphorus pentachlorideHCID 58941863N-(3-cyanophenyl)-4-methyl-1,2,5-oxadiazole-3-carboxamide

Product 1

HCID 178434783HCID 178434783, compoundYield 10.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

N-(3-Cyanophenyl)-4-methyl-1,2,5-oxadiazole-3-carboxamide (25 mg, 0.11 mmol) was suspended in benzene (2 mL) under an atmosphere of nitrogen. Phosphorus pentachloride (25 mg, 0.12 mmol) was added and the solution was heated at reflux for 2.5 hrs. The reaction was then evaporated to dryness. The crude was dissolved in EtOH (1.6 mL) and hydroxylamine (200 μL, 3 mmol, 50% solution in water) was added to the reaction. The crude was purified by preparative LCMS to afford the desired product (2.9 mg). MF═C11H9N5O2; LCMS calculated for C11H9N5O2 (M+H)+: m/z=244.1.

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for 2.5 hrs
  3. customThe reaction was then evaporated to dryness
  4. dissolutionThe crude was dissolved in EtOH (1.6 mL)
  5. customThe crude was purified by preparative LCMS

Sources & evidence

ORD record
ord-83b791514f8240a9bc80c29fd429b550
Source dataset
uspto-grants-2013_05
Patent number
US08450351B2

Reaction notes

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