Hydrochloric Acid → HCID 178428875, compound

HRID 1168667Notes

Reaction equation

HRID 1168667 reaction equation
CC(C)([O-])C.[K+].[CH3:7][C:8]1[C:25]([C:26]2[CH2:30][CH:29]([CH2:31]Cl)[O:28][N:27]=2)=[C:24]([S:33]([CH3:36])(=[O:35])=[O:34])[CH:23]=[CH:22][C:9]=1[C:10]([C:12]1[CH:13]=[N:14][N:15]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:16]=1[OH:17])=[O:11].Cl>CS(C)=O>[CH3:7][C:8]1[C:25]([C:26]2[CH:30]3[CH:29]([CH2:31]3)[O:28][N:27]=2)=[C:24]([S:33]([CH3:36])(=[O:35])=[O:34])[CH:23]=[CH:22][C:9]=1[C:10]([C:12]1[CH:13]=[N:14][N:15]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:16]=1[OH:17])=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 178428876HCID 178428876, compound

Product 1

HCID 178428875HCID 178428875, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

At room temperature, 0.17 g (1.50 mmol) of potassium tert-butoxide was added to a solution of 0.23 g (0.51 mmol) of 4-[2-methyl-3-(5-chloromethyl-4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoyl]-5-hydroxy-1-tert-butyl-1H-pyrazole in 2.5 ml of dimethyl sulfoxide, and the mixture was stirred overnight. The mixture was then stirred into 300 ml of 3% strength aqueous hydrochloric acid, the aqueous phase was extracted three times with in each case 200 ml of ethyl acetate and the combined organic phases were washed four times with in each case 50 ml of water, dried over sodium sulfate and concentrated under reduced pressure. This gave 0.12 g (57%) of the title compound in the form of a brown solid of melting point 69-74° C.

Workup

  1. extractionthe aqueous phase was extracted three times with in each case 200 ml of ethyl acetate
  2. washthe combined organic phases were washed four times with in each case 50 ml of water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5b235736081847eca316f7533a3179ac
Source dataset
uspto-grants-2003_09
Patent number
US06627581B1

Reaction notes

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