Potassium Carbonate → HCID 9888801, compound

HRID 969964Notes

Reaction equation

HRID 969964 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][C:8]1[C:13]([C:14]([OH:16])=O)=[CH:12][N:11]=[C:10]([CH3:17])[CH:9]=1.[F:18][C:19]([F:37])([F:36])[C:20]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[N:22]([C:29]2[CH:35]=[CH:34][C:32]([NH2:33])=[CH:31][CH:30]=2)[N:21]=1.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[CH3:7][C:8]1[C:13]([C:14]([NH:33][C:32]2[CH:31]=[CH:30][C:29]([N:22]3[C:23]([C:25]([F:26])([F:27])[F:28])=[CH:24][C:20]([C:19]([F:37])([F:36])[F:18])=[N:21]3)=[CH:35][CH:34]=2)=[O:16])=[CH:12][N:11]=[C:10]([CH3:17])[CH:9]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 65578Oxalyl chlorideHCID 8172904,6-dimethylnicotinic acidHCID 27406684-(3,5-Bis(trifluoromethyl)-1H-pyrazol-1-yl)aniline

Product 1

HCID 9888801HCID 9888801, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
17.5 °C

Procedure

Oxalyl chloride (8.7 ml) was added to a mixture of 4,6-dimethylnicotinic acid (15.1 g) and dichloromethane (150 ml) under ice cooling, followed by stirring at 15 to 20° C. for one hour. A mixture of 4-[3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl]aniline (23.59 g) and dichloromethane (300 ml) was added to the resulting reaction solution, followed by stirring at room temperature for 18 hours. An aqueous 20% potassium carbonate solution (about 200 ml) was added to the reaction solution, from which the organic layer was separated. Subsequently, the aqueous layer was extracted with dichloromethane (about 50 ml). The organic layer and the extract solution were combined together and subsequently concentrated under reduced pressure. The resulting residue was recrystallized from a mixed solvent (270 ml) of ethanol and water (2:1, respectively), to obtain 4,6-dimethyl-4′-[3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl]nicotinanilide (26.70 g) as bluish white solid.

Workup

  1. additionwas added to the resulting reaction solution
  2. stirringby stirring at room temperature for 18 hours
  3. customwas separated
  4. extractionSubsequently, the aqueous layer was extracted with dichloromethane (about 50 ml)
  5. concentrationsubsequently concentrated under reduced pressure
  6. customThe resulting residue was recrystallized from a mixed solvent (270 ml) of ethanol and water (2:1

Sources & evidence

ORD record
ord-6255f8ac63414692b961ccda4b7c78ae
Source dataset
uspto-grants-2007_12
Patent number
US07309710B2

Reaction notes

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