Oxygen → HCID 118022955, compound

HRID 929314Notes

Reaction equation

HRID 929314 reaction equation
[Cl:1][C:2]1[C:6]([N:7]([CH2:15][CH3:16])[C:8](=[O:14])[CH:9]([CH3:13])[CH2:10][CH:11]=C)=[CH:5][N:4]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[N:3]=1.[O:23]=[O+][O-].O=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl.CO>[Cl:1][C:2]1[C:6]([N:7]([CH2:15][CH3:16])[C:8](=[O:14])[CH:9]([CH3:13])[CH2:10][CH:11]=[O:23])=[CH:5][N:4]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[N:3]=1

Participants

7

Reactant 4

HCID 977OxygenHCID 11776TriphenylphosphineHCID 24823OzoneHCID 118023088HCID 118023088, compound

Product 1

HCID 118022955HCID 118022955, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To N-(3-Chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-2-methylpent-4-enamide (0.450 g, 1.41 mmol) in a flask with a stir bar dissolved in CH2Cl2 (13 mL) and MeOH (1.3 mL) was added Sudan III indicator solution (0.01 M, 0.060 mL). The flask was attached to an ozone generator and a flow of oxygen was initiated, with stirring. The reaction was cooled to −78° C., and the ozone production was bubbled through the solution for approxmately 6 minutes before the pink color was absent and the yellow solution started to turn green/blue. The ozone generation was arrested, and pure oxygen was bubbled through the reaction for approximately 5 minutes as the dark colors faded and the yellow color became prominent. While still at −78° C., triphenylphosphine (0.555 g, 2.12 mmol) was added as a solid, and the cooling bath was removed. A nitrogen gas inlet was attached to the flask, and the reaction was allowed to warm slowly to room temperature. The product was then concentrated and loaded onto CELITE®. Purification by flash column chromatography using 0-40% acetone/hexanes provided the title compound as a clear yellow oil that crystallized upon standing (0.390 g, 73%).

Workup

  1. customthe ozone production was bubbled through the solution for approxmately 6 minutes before the pink color
  2. custompure oxygen was bubbled through the reaction for approximately 5 minutes as the dark colors
  3. customthe cooling bath was removed
  4. customA nitrogen gas inlet was attached to the flask
  5. temperatureto warm slowly to room temperature
  6. concentrationThe product was then concentrated
  7. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-50ef465354904a96aa402ad231bd2315
Source dataset
uspto-grants-2016_03
Patent number
US09295260B2

Reaction notes

Loading…