Potassium Carbonate → HCID 178422822, compound

HRID 1276139Notes

Reaction equation

HRID 1276139 reaction equation
[Cl:1][C:2]1[C:10]([C:11]2[O:15][N:14]=[C:13]([CH3:16])[CH:12]=2)=[C:9]([Cl:17])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[OH:18][C:19]1[N:23]([CH3:24])[N:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>C(COC)OC>[Cl:1][C:2]1[C:10]([C:11]2[O:15][N:14]=[C:13]([CH3:16])[CH:12]=2)=[C:9]([Cl:17])[CH:8]=[CH:7][C:3]=1[C:4]([C:20]1[CH:21]=[N:22][N:23]([CH3:24])[C:19]=1[OH:18])=[O:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 22114946HCID 22114946, compoundHCID 178481816HCID 178481816, compound

Product 1

HCID 178422822HCID 178422822, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

At 0 to 5° C., the 2,4-dichloro-3-(3-methylisoxazol-5-yl)benzoyl chloride obtained above (step e) in 40 ml of dimethoxyethane was added to 0.7 g (7.35 mmol) of 5-hydroxy-1-methyl-1H-pyrazole in 30 ml of dimethoxyethane and 2.0 g (14.7 mmol) of potassium carbonate. The mixture was stirred at room temperature for 3.5 hours, heated under reflux for 1 hour and stirred at room temperature for 12 hours. The precipitate that had formed was filtered off with suction and introduced into 50 ml of water. The mixture is acidified to pH=1 and the solid is filtered off with suction and dried. Likewise, the first-mentioned filtrate was taken up in 400 ml of water, washed with methyl t-butyl ether, adjusted to pH 3 and extracted with methylene chloride. The combined organic phases were dried and concentrated. 1.9 g (73% of theory) of 4-[2,4-dichloro-3-(3-methylisoxazol-5-yl)benzoyl]-5-hydroxy-1-methyl-1H-pyrazole were obtained.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 hour
  3. stirringstirred at room temperature for 12 hours
  4. customThe precipitate that had formed
  5. filtrationwas filtered off with suction
  6. additionintroduced into 50 ml of water
  7. filtrationthe solid is filtered off with suction
  8. customdried
  9. washwashed with methyl t-butyl ether
  10. extractionextracted with methylene chloride
  11. customThe combined organic phases were dried
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-8abe4e43a2e34c3f9565c78195577983
Source dataset
uspto-grants-2000_12
Patent number
US06165944

Reaction notes

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