Water → HCID 178434738, compound

HRID 859096Notes

Reaction equation

HRID 859096 reaction equation
[Cl:1][C:2]1[C:10]([CH:11]2[O:15][N:14]=[C:13]([CH3:16])[CH2:12]2)=[C:9]([S:17]([CH3:20])(=[O:19])=[O:18])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[OH:21][C:22]1[N:26]([CH3:27])[N:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].O>C(COC)OC>[Cl:1][C:2]1[C:10]([CH:11]2[O:15][N:14]=[C:13]([CH3:16])[CH2:12]2)=[C:9]([S:17]([CH3:20])(=[O:19])=[O:18])[CH:8]=[CH:7][C:3]=1[C:4]([C:23]1[CH:24]=[N:25][N:26]([CH3:27])[C:22]=1[OH:21])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium Carbonate2×HCID 11221369HCID 11221369, compoundHCID 178481816HCID 178481816, compound

Product 1

HCID 178434738HCID 178434738, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

At 0–5° C., a solution of 6.7 g (20 mmol) of 2-chloro-3-(3-methyl-4,5-dihydroisoxazol-5-yl)-4-methylsulfonylbenzoyl chloride in 80 ml of dimethoxyethane was added dropwise to a solution of 2.0 g (20 mmol) of 5-hydroxy-1-methylpyrazole and 3.3 g (24 mmol) of potassium carbonate in 30 ml of anhydrous dimethoxyethane. After 12 hours of stirring at room temperature, a further 8.2 g (60 mmol) of potassium carbonate were added, and the batch was refluxed for six hours. After cooling, the reaction mixture was stirred into 1 l of water and extracted with methylene chloride. The aqueous phase was then adjusted to pH 4 using 10% strength hydrochloric acid and extracted repeatedly with methylene chloride, with readjustment of the pH. The organic phase was dried and the solvent removed, giving 5.3 g (13 mmol, 67%) of the desired compound.

Workup

  1. temperaturethe batch was refluxed for six hours
  2. temperatureAfter cooling
  3. extractionextracted with methylene chloride
  4. extractionextracted repeatedly with methylene chloride, with readjustment of the pH
  5. customThe organic phase was dried
  6. customthe solvent removed

Sources & evidence

ORD record
ord-f2db9614b85c48c1bee038be38d996a2
Source dataset
uspto-grants-2006_12
Patent number
US07151075B2

Reaction notes

Loading…