Dimethylformamide → HCID 66958664, compound

HRID 2283810Notes

Reaction equation

HRID 2283810 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]([OH:20])=O)=[N:6]1)[CH2:2][CH2:3][CH3:4].C(Cl)(=O)C(Cl)=O.C[N:28](C=O)C>ClCCl>[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]([NH2:28])=[O:20])=[N:6]1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 66958955HCID 66958955, compound

Product 1

HCID 66958664HCID 66958664, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-butyl-5-[2-(propylsulfonyl)ethyl]-1H-pyrazole-3-carboxylic acid (4.00 g, 13.22 mmol) in dichloromethane (66 mL) was added oxalyl chloride (3.5 mL, 39.7 mmol) and a drop of DMF. The solution bubbled vigorously and was stirred at ambient temperature for 30 minutes. The solution was concentrated under reduced pressure. The residue was dissolved in dichloromethane (66 mL) and the resulting solution was cooled in an ice bath, then concentrated ammonium hydroxide (66 mL) was added dropwise. After the addition was complete, the ice bath was removed and the mixture was stirred at ambient temperature for 2 hours. The volatiles were removed under reduced pressure to afford a slurry that was extracted with chloroform (2×100 mL). The organic layers were combined and concentrated under reduced pressure to afford 4.0 g of 1-butyl-5-[2-(propylsulfonyl)ethyl]-1H-pyrazole-3-carboxamide as a white solid.

Workup

  1. customThe solution bubbled vigorously
  2. concentrationThe solution was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in dichloromethane (66 mL)
  4. temperaturethe resulting solution was cooled in an ice bath
  5. additionconcentrated ammonium hydroxide (66 mL) was added dropwise
  6. additionAfter the addition
  7. customthe ice bath was removed
  8. stirringthe mixture was stirred at ambient temperature for 2 hours
  9. customThe volatiles were removed under reduced pressure
  10. customto afford a slurry that
  11. extractionwas extracted with chloroform (2×100 mL)
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1d357d6fc8bc438a95c77933e9086a72
Source dataset
uspto-grants-2015_09
Patent number
US09145410B2

Reaction notes

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