Hydrogen Peroxide → HCID 23346250, compound

HRID 1856202Notes

Reaction equation

HRID 1856202 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](=[O:27])[CH2:11][CH2:12][N:13]2[CH2:18][CH:17]=[C:16]([S:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH2:15][CH2:14]2)=[CH:5][CH:4]=1.OO.[C:30]([OH:39])(=[O:38])[CH:31]([CH:33]([C:35]([OH:37])=[O:36])[OH:34])[OH:32]>C(O)(=O)C>[OH:34][CH:33]([CH:31]([OH:32])[C:30]([OH:39])=[O:38])[C:35]([OH:37])=[O:36].[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](=[O:27])[CH2:11][CH2:12][N:13]2[CH2:14][CH:15]=[C:16]([S:19]([C:20]3[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=3)=[O:32])[CH2:17][CH2:18]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 8752,3-Dihydroxybutanedioic AcidHCID 70595031HCID 70595031, compound

Product 1

HCID 23346250HCID 23346250, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 10.0 g of 1-(4-fluorophenyl)-4-{4-[(4-fluorophenyl)thio]-1,2,3,6-tetrahydro-1-pyridinyl}butanone hydrochloride in 75 ml of glacial acetic acid at room temperature is added dropwise a solution of 2.77 g of 30% hydrogen peroxide in 25 ml of acetic acid over 20 minutes. The solution is allowed to stand at room temperature for 48 hours after which the solvent is removed in vacuo. The residue is neutralized with aqueous sodium bicarbonate, and the product is extracted into methylene chloride. The organic extracts is dried over anhydrous sodium sulfate and evaporated to give an orange oil. The oil is treated with methanolic tartaric acid. Crystallization is induced, and the product is collected to yield 9.00 g (66.2%) of white powder, m.p. 151°-154° C. Recrystallization from methanol gives white crystals, m.p. 154°-155° C.

Workup

  1. customafter which the solvent is removed in vacuo
  2. extractionthe product is extracted into methylene chloride
  3. dry with materialThe organic extracts is dried over anhydrous sodium sulfate
  4. customevaporated
  5. customto give an orange oil
  6. customCrystallization
  7. customthe product is collected

Sources & evidence

ORD record
ord-83ff22c11f81454e80dd86351b221348
Source dataset
uspto-grants-1980_08
Patent number
US04218455

Reaction notes

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