Phosphorus oxychloride → HCID 66958443, compound

HRID 2283811Notes

Reaction equation

HRID 2283811 reaction equation
[CH2:1]([N:5]1[C:9]([CH2:10][CH2:11][S:12]([CH2:15][CH2:16][CH3:17])(=[O:14])=[O:13])=[CH:8][C:7]([C:18]([NH2:20])=O)=[N:6]1)[CH2:2][CH2:3][CH3:4].P(Cl)(Cl)(Cl)=O>C1(C)C=CC=CC=1>[CH2:1]([N:5]1[C:9]([CH2:10][CH2:11][S:12]([CH2:15][CH2:16][CH3:17])(=[O:14])=[O:13])=[CH:8][C:7]([C:18]#[N:20])=[N:6]1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 66958664HCID 66958664, compound

Product 1

HCID 66958443HCID 66958443, compoundYield 101%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-Butyl-5-[2-(propylsulfonyl)ethyl]-1H-pyrazole-3-carboxamide (4.00 g, 13.27 mmol) in toluene (66 mL) was treated with phosphorous oxychloride (2.50 mL, 26.5 mmol). The solution was heated at reflux for 1 hour. The reaction mixture was allowed to cool to ambient temperature and the volatiles were removed under reduced pressure. The resulting oil was diluted with water (50 mL) and saturated aqueous sodium bicarbonate. The mixture was extracted with dichloromethane (2×50 mL). The organic layers were combined, washed with saturated aqueous sodium bicarbonate (50 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure to provide 3.8 g of 1-butyl-5-[2-(propylsulfonyl)ethyl]-1H-pyrazole-3-carbonitrile as a brown oil.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 1 hour
  3. customthe volatiles were removed under reduced pressure
  4. additionThe resulting oil was diluted with water (50 mL) and saturated aqueous sodium bicarbonate
  5. extractionThe mixture was extracted with dichloromethane (2×50 mL)
  6. washwashed with saturated aqueous sodium bicarbonate (50 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a91f4dda13b641c488332d434586d9ab
Source dataset
uspto-grants-2015_09
Patent number
US09145410B2

Reaction notes

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