Phosphorus oxychloride → HCID 178506285, compound

HRID 719295Notes

Reaction equation

HRID 719295 reaction equation
[C:1]1([C:7]2[NH:11][N:10]=[C:9]([C:12]([F:15])([F:14])[F:13])[C:8]=2[NH:16][C:17](=O)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)(Cl)=O>[N+](C1C=CC=CC=1)([O-])=O>[C:18]1([C:17]2[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=3[C:7]3[NH:11][N:10]=[C:9]([C:12]([F:15])([F:14])[F:13])[C:8]=3[N:16]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178522275HCID 178522275, compound

Product 1

HCID 178506285HCID 178506285, compound

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Conditions

Temperature
185 °C

Procedure

A mixture of 1.02 g of N-(5-phenyl-3-trifluoromethyl-1H-pyrazol-4-yl)-benzamide in 10 mL of nitrobenzene was treated with 0.41 mL of phosphorous oxychloride and stirred at 185° C. for 6 h. The solvent was distilled off under high vacuum and the residue was partitioned between ethyl acetate and water. The organic portion was washed with saturated sodium bicarbonate, water and brine and dried over magnesium sulphate. Concentration and purification by MPLC, eluting with 1/3 ethyl acetate/heptane, gave the title compound as a white solid, melting point 264–265° C.

Workup

  1. distillationThe solvent was distilled off under high vacuum
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe organic portion was washed with saturated sodium bicarbonate, water and brine
  4. dry with materialdried over magnesium sulphate
  5. concentrationConcentration and purification by MPLC
  6. washeluting with 1/3 ethyl acetate/heptane

Sources & evidence

ORD record
ord-43cc9e82328e40d4ae3f30dae264ec5e
Source dataset
uspto-grants-2006_11
Patent number
US07132428B2

Reaction notes

Loading…