Sodium Hydroxide → HCID 86616009, compound

HRID 2243471Notes

Reaction equation

HRID 2243471 reaction equation
P([O-])(O)(O)=O.[Na+].[OH-].[Na+].[Cl:9][C:10]1[C:11]([N:16]2[C:20]([S:21]([O-:23])=[O:22])=[CH:19][C:18]([C:24]([F:27])([F:26])[F:25])=[N:17]2)=[N:12][CH:13]=[CH:14][CH:15]=1.[Li+].ClN1C(=[O:35])CCC1=O>O.C(OCC)(=O)C>[Cl:9][C:10]1[C:11]([N:16]2[C:20]([S:21]([OH:35])(=[O:23])=[O:22])=[CH:19][C:18]([C:24]([F:27])([F:25])[F:26])=[N:17]2)=[N:12][CH:13]=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 31398ChlorosuccinimideHCID 23672064Monosodium phosphateHCID 68545974Lithium 1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-sulfinate

Product 1

HCID 86616009HCID 86616009, compoundYield 78.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 100 mL of pH 6 buffer (prepared by dissolving 1.2 g (10 mmol) of sodium dihydrogenphosphate in 100 mL of water and adding 11.2 mL of 1N sodium hydroxide) was added 3.52 g (11.1 mmol) of the title material from Step B. This solution was cooled in an ice bath and 75 mL of ethyl acetate and 1.48 g (11.1 mmol) of N-chlorosuccinimide were added. After 30 minutes the layers were separated. The organic layer was dried (sodium sulfate) and the solvent was removed with a rotary evaporator. To the residue was added carbon tetrachloride and the solids were removed by filtration. The solvent was removed from the filtrate with a rotary evaporator to afford 2.84 g of the title compound as an amber oil. 1HNMR(CDCl3) δ 7.45 (s, 1H), 7.58 (dd, 1h), 8.01 (dd, 1h), 8.58 (dd, 1h).

Workup

  1. temperatureThis solution was cooled in an ice bath
  2. customAfter 30 minutes the layers were separated
  3. dry with materialThe organic layer was dried (sodium sulfate)
  4. customthe solvent was removed with a rotary evaporator
  5. additionTo the residue was added carbon tetrachloride
  6. customthe solids were removed by filtration
  7. customThe solvent was removed from the filtrate with a rotary evaporator

Sources & evidence

ORD record
ord-eb3921688f9549afaa64f8c93b1a7ae3
Source dataset
uspto-grants-2010_03
Patent number
US07674936B2

Reaction notes

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