Potassium Carbonate → HCID 178440455, compound

HRID 1276130Notes

Reaction equation

HRID 1276130 reaction equation
[Cl:1][C:2]1[C:10]([C:11]2[O:15][N:14]=[C:13]([CH:16]([CH3:18])[CH3:17])[N:12]=2)=[C:9]([Cl:19])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[OH:20][C:21]1[N:25]([CH3:26])[N:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>C(COC)OC.O>[Cl:1][C:2]1[C:10]([C:11]2[O:15][N:14]=[C:13]([CH:16]([CH3:18])[CH3:17])[N:12]=2)=[C:9]([Cl:19])[CH:8]=[CH:7][C:3]=1[C:4]([C:22]1[CH:23]=[N:24][N:25]([CH3:26])[C:21]=1[OH:20])=[O:5]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 22114927HCID 22114927, compoundHCID 178481816HCID 178481816, compound

Product 1

HCID 178440455HCID 178440455, compoundYield 79.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

At 5-10° C., 2.00 g (6.3 mmol) of 2,4-dichloro-3-(3-i-propyl-1,2,4-oxadiazol-5-yl)benzoyl chloride in 10 ml of dimethoxyethane were added dropwise to 0.62 g (6.3 mmol) of 5-hydroxy-1-methyl-1H-pyrazole and 1.74 g (12.6 mmol) of potassium carbonate in 20 ml of dimethoxyethane. After 2.5 hours of stirring at room temperature, the mixture was heated under reflux for 2 hours and then once more stirred at room temperature for 12 hours. The reaction mixture was then taken up in water and washed with methylene chloride or toluene; the aqueous phase that remained was adjusted to pH=3 using hydrochloric acid and the precipitate that had formed was filtered off with suction and dried. 1.90 g (79% of theory) of 4-[2,4-dichloro-3-(3-i-propyl-1,2,4-oxadiazol-5-yl)benzoyl]-5-hydroxy-1-methyl-1H-pyrazole were obtained.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. stirringonce more stirred at room temperature for 12 hours
  4. washwashed with methylene chloride or toluene
  5. customthe precipitate that had formed
  6. filtrationwas filtered off with suction
  7. customdried

Sources & evidence

ORD record
ord-d8be8795f998411cb8fa62c4de1b55d8
Source dataset
uspto-grants-2000_12
Patent number
US06165944

Reaction notes

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