Ammonium Chloride → 5-(3-benzenesulfonylpropyl)-1-butyl-1H-pyrazole-3-carboxamide

HRID 1984471Notes

Reaction equation

HRID 1984471 reaction equation
C(Cl)(=O)C(Cl)=O.[C:7]1([S:13]([CH2:16][CH2:17][CH2:18][C:19]2[N:23]([CH2:24][CH2:25][CH2:26][CH3:27])[N:22]=[C:21]([C:28]([OH:30])=O)[CH:20]=2)(=[O:15])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Cl-].[NH4+:32]>ClCCl.CN(C=O)C>[C:7]1([S:13]([CH2:16][CH2:17][CH2:18][C:19]2[N:23]([CH2:24][CH2:25][CH2:26][CH3:27])[N:22]=[C:21]([C:28]([NH2:32])=[O:30])[CH:20]=2)(=[O:15])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 65578Oxalyl chlorideHCID 669583705-(3-benzenesulfonylpropyl)-1-butyl-1H-pyrazole-3-carboxylic acid

Product 1

HCID 669590245-(3-benzenesulfonylpropyl)-1-butyl-1H-pyrazole-3-carboxamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneCatalystHCID 6228DimethylformamideSolvent

Procedure

Oxalyl chloride (7.8 mL, 90.0 mmol) was added slowly via syringe to a solution of 5-(3-benzenesulfonylpropyl)-1-butyl-1H-pyrazole-3-carboxylic acid (10.5 g, 30.0 mmol) in 100 mL of dichloromethane containing one drop of DMF. After 2 hours of stirring, saturated ammonium chloride (100 mL) was added to the reaction mixture and the reaction was maintained for 1 hour. The reaction mixture was concentrated under reduced pressure, diluted with dichloromethane and washed with water. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and concentrated to afford 10.4 g of 5-(3-benzenesulfonylpropyl)-1-butyl-1H-pyrazole-3-carboxamide.

Workup

  1. temperaturethe reaction was maintained for 1 hour
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additiondiluted with dichloromethane
  4. washwashed with water
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-90bd407d803d41cbb4ed419c69022936
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

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