Water → HCID 178434737, compound

HRID 859097Notes

Reaction equation

HRID 859097 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]([CH:27]2[CH2:29][CH2:28]2)[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]([CH:27]2[CH2:29][CH2:28]2)[C:22]=1[OH:21])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium Carbonate2×HCID 11221369HCID 11221369, compoundHCID 178516539HCID 178516539, compound

Product 1

HCID 178434737HCID 178434737, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

At 0–5° C., a solution of 1.0 g (3 mmol) of 2-chloro-3-(3-methyl-4,5-dihydroisoxazol-5-yl)-4-methylsulfonylbenzoyl chloride in 50 ml of dimethoxyethane was added dropwise to a solution of 0.47 g (3 mmol) of 5-hydroxy-1-cyclopropylpyrazole and 0.5 g (3.6 mmol) of potassium carbonate in 36 ml of anhydrous dimethoxyethane. After 12 hours of stirring at room temperature, a further 1.0 g (7.2 mmol) of potassium carbonate were added and the batch was refluxed for 6 hours. After cooling, the reaction mixture was stirred into 600 ml of water and extracted with methylene chloride. The aqueous phase was then adjusted to pH 4 using 10% strength hydrochloric acid and extracted with methylene chloride. Drying of the organic phase and removal of the solvent gave 0.8 g (1.8 mmol, 63%) of the desired compound.

Workup

  1. temperaturethe batch was refluxed for 6 hours
  2. temperatureAfter cooling
  3. extractionextracted with methylene chloride
  4. extractionextracted with methylene chloride
  5. customDrying of the organic phase and removal of the solvent

Sources & evidence

ORD record
ord-6e51e688e63d48309d723d848ca5bccb
Source dataset
uspto-grants-2006_12
Patent number
US07151075B2

Reaction notes

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