Phosphorus oxide (P4O10) → HCID 178434206, compound

HRID 719277Notes

Reaction equation

HRID 719277 reaction equation
[CH3:1][C:2]1[C:6]([NH:7][C:8]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)=O)=[C:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[NH:4][N:3]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>P(Cl)(Cl)(Cl)=O>[CH3:1][C:2]1[C:6]2[N:7]=[C:8]([C:10]3[S:11][CH:12]=[CH:13][CH:14]=3)[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[C:5]=2[NH:4][N:3]=1

Participants

4

Reactant 2

HCID 14812Phosphorus oxide (P4O10)HCID 178434579HCID 178434579, compound

Product 1

HCID 178434206HCID 178434206, compound

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
120 °C

Procedure

To a suspension of 682.4 mg of thiophene-2-carboxylic acid (3-methyl-5-phenyl-1H-pyrazol-4-yl)-amide in 11.0 mL of phosphorous oxychloride was added 5.00 g of phosphorous pentoxide and the resulting suspension was heated at 120° C. for 5 h. The reaction mixture was cooled to rt and quenched with the addition of ice and water and then neutralized with solid sodium carbonate. The aqueous mixture was extracted with ethyl acetate and the combined organic extracts were washed with brine, dried (magnesium sulfate) and concentrated under reduced pressure. The residue was purified by means of MPLC (4 g SiO2, 30% ethyl acetate:dichloromethane) to give the title compound as a tan solid.

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. customquenched with the addition of ice and water
  3. extractionThe aqueous mixture was extracted with ethyl acetate
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by means of MPLC (4 g SiO2, 30% ethyl acetate:dichloromethane)

Sources & evidence

ORD record
ord-7977dd3d0f18496584b584c775d8f04e
Source dataset
uspto-grants-2006_11
Patent number
US07132428B2

Reaction notes

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