Hydroxylamine → HCID 178434783, compound

HRID 1845753Notes

Reaction equation

HRID 1845753 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 C11H10N5O2 (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-a6f41a3259cc4c6fa52eabc568941c7d
Source dataset
uspto-grants-2015_02
Patent number
US08951536B2

Reaction notes

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