Hydroxylamine → HCID 178425378, compound

HRID 1891412Notes

Reaction equation

HRID 1891412 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:24])=[C:6]([CH:23]=1)[CH2:7][NH:8][C:9]([C:11]1[O:15][N:14]=[C:13]([NH:16]C(=O)C(F)(F)F)[CH:12]=1)=O.P(Cl)(Cl)(Cl)(Cl)Cl.C1(C)C=CC=CC=1.[NH2:38][OH:39]>C(O)C.O.C(OCC)(=O)C>[NH2:16][C:13]1[CH:12]=[C:11]([C:9](=[N:38][OH:39])[NH:8][CH2:7][C:6]2[CH:23]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[CH3:24])[O:15][N:14]=1

Participants

8

Reactant 4

HCID 787HydroxylamineHCID 1140TolueneHCID 24819Phosphorus pentachlorideHCID 59799402HCID 59799402, compound

Product 1

HCID 178425378HCID 178425378, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

N-(5-chloro-2-methylbenzyl)-3-[(trifluoroacetyl)amino]isoxazole-5-carboxamide (550 mg, 1.5 mmol) and phosphorus pentachloride (620 mg, 3.0 mmol) were weighed into a vial. Toluene (18 mL) was added and the vial was heated at 90° C. for 1.5 h. The solution was stripped to dryness and residue was dissolved in ethanol (14 mL) and 50% hydroxylamine in water (3.1 mL) was added. After stirring for 0.5 h, reaction was diluted with ethyl acetate and water. Aqueous layer was extracted with ethyl acetate once. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated to give the desired product (570 mg, 100%). LCMS calculated for C14H13ClF3N4O3(M+H)+: m/z=377.1.

Workup

  1. customreaction
  2. extractionAqueous layer was extracted with ethyl acetate once
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0824c1491fbf40f998ff6528ce8baf73
Source dataset
uspto-grants-2013_08
Patent number
US08507541B2

Reaction notes

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