Dichloromethane → HCID 15334491, compound

HRID 260971Notes

Reaction equation

HRID 260971 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([C:12]2[C:16]([Cl:17])=[C:15]([C:18]([F:21])([F:20])[F:19])[N:14]([CH3:22])[N:13]=2)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:23](Cl)(=O)[C:24](Cl)=O.[CH2:29](Cl)Cl>CN(C=O)C>[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([C:12]2[C:16]([Cl:17])=[C:15]([C:18]([F:20])([F:19])[F:21])[N:14]([CH3:22])[N:13]=2)=[CH:7][C:3]=1[C:4]([O:6][CH:23]([CH3:24])[CH3:29])=[O:5]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 15334490HCID 15334490, compound

Product 1

HCID 15334491HCID 15334491, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Conditions

Temperature
60 °C

Procedure

To a solution of 4.3 g (0.012 mole) 2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-4-fluorobenzoic acid in 50 mL methylene chloride was added 3.1 mL (0.036 mole) oxalyl chloride causing the evolution of gas. When this evolution ceased, one drop of DMF was added and the solution stirred until the gas evolution ceased. The solution was concentrated in vacuo and the resultant residue dissolved in 25 mL isopropanol and heated to 60° C. for 1 hour. The solution was cooled, poured into 200 mL cold water and the solid filtered and dried. The product was recrystallized from ethanol/water to yield 1.69 g (70%) of 2-chloro-5-[4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]-4-fluorobenzoic acid, 1-methylethyl ester as a white solid; mp 69° C.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. dissolutionthe resultant residue dissolved in 25 mL isopropanol
  3. temperatureThe solution was cooled
  4. additionpoured into 200 mL cold water
  5. filtrationthe solid filtered
  6. customdried
  7. customThe product was recrystallized from ethanol/water

Sources & evidence

ORD record
ord-68ba6e98f76e4846a9348138c0ac2bcb
Source dataset
uspto-grants-1996_06
Patent number
US05530126

Reaction notes

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