Sodium Sulfate → HCID 22461196, compound

HRID 1937450Notes

Reaction equation

HRID 1937450 reaction equation
[C:1]([C:4]1[C:8]([S:9]([CH3:12])(=[O:11])=[O:10])=[C:7]([NH2:13])[N:6]([C:14]2[C:19]([Cl:20])=[CH:18][C:17]([C:21]([F:24])([F:23])[F:22])=[CH:16][C:15]=2[Cl:25])[N:5]=1)(=[O:3])[CH3:2].[SH:26][CH:27](O)[CH3:28].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCOCC1.[Cl-].[Zn+2].[Cl-]>[NH2:13][C:7]1[N:6]([C:14]2[C:15]([Cl:25])=[CH:16][C:17]([C:21]([F:23])([F:22])[F:24])=[CH:18][C:19]=2[Cl:20])[N:5]=[C:4]([C:1]2([CH3:2])[S:26][CH2:27][CH2:28][O:3]2)[C:8]=1[S:9]([CH3:12])(=[O:10])=[O:11]

Participants

6

Reactant 3

HCID 24436Sodium SulfateHCID 4713212Mercapto-ethanolHCID 15457441HCID 15457441, compound

Product 1

HCID 22461196HCID 22461196, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 54.34 grams (0.131 mole) of 3-acetyl-5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfonyl-1H-pyrazole in 500 mL of dioxane was added, in sequence, 36.7 mL (0.522 mole) of mercaptoethanol, 71.1 grams (0.522 mole) of anhydrous zinc chloride and 62.1 grams (0.522 mole) of anhydrous sodium sulfate while cooling at 0° C. in an ice bath. The mixture was then stirred for a period of approximately 17 hours while allowing it to warm to room temperature. The mixture was filtered to remove salts and the filtrate concentrated under reduced pressure and diluted with 40 mL of acetonitrile, collecting the product by filtering at 35° C. The filtrate was further diluted with acetonitrile to obtain a second crop of product. The combined crops of 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-3-(2-methyl-1,3-oxathiolane-2-yl)-4-methylsulfonyl-1H-pyrazole gave 30.53 grams of material, having a melting point of 201° C. This compound is hereinafter referred to as Compound No. 23.

Workup

  1. temperatureto warm to room temperature
  2. filtrationThe mixture was filtered
  3. customto remove salts
  4. concentrationthe filtrate concentrated under reduced pressure
  5. additiondiluted with 40 mL of acetonitrile
  6. customcollecting the product
  7. filtrationby filtering at 35° C
  8. additionThe filtrate was further diluted with acetonitrile
  9. customto obtain a second crop of product

Sources & evidence

ORD record
ord-7a771bfe757342118a046f9f33d6f34e
Source dataset
uspto-grants-2002_05
Patent number
US06395760B1

Reaction notes

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