m-Chloroperbenzoic acid → HCID 18327518, compound

HRID 1250200Notes

Reaction equation

HRID 1250200 reaction equation
[CH3:1][C:2]1[N:3]=[N:4][S:5][C:6]=1[CH2:7]SC1C=CC=CC=1.Cl[C:16]1[CH:21]=[CH:20][CH:19]=[C:18](C(OO)=O)[CH:17]=1.[S:26]([O-:29])(O)=[O:27].[Na+]>C(Cl)Cl>[CH3:1][C:2]1[N:3]=[N:4][S:5][C:6]=1[CH2:7][S:26]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)(=[O:29])=[O:27]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 159066404-Methyl-5-[(phenylthio)methyl]-1,2,3-thiadiazoleHCID 23665763Sodium Bisulfite

Product 1

HCID 18327518HCID 18327518, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 5.0 ml of methylene chloride was dissolved 0.20 g (0.99 mmol) of 4-methyl-5-phenylthiomethyl-1,2,3-thiadiazole. Then, 0.40 g (2.3 mmol) of m-chloroperbenzoic acid was added to the solution obtained above, and was stirred for 20 hours at room temperature. Then, an aqueous solution of sodium hydrogen sulfite was added to the reaction mixture to stop the reaction, the objective product was extracted with ethyl acetate, the organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography using 2:1 mixture of n-hexane and ethyl acetate. Thus, 0.23 g of the objective compound was obtained.

Workup

  1. customobtained above, and
  2. customthe reaction
  3. extractionthe objective product was extracted with ethyl acetate
  4. washthe organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography
  7. addition2:1 mixture of n-hexane and ethyl acetate

Sources & evidence

ORD record
ord-3abf5fbcfd964527af4d43dc92c52746
Source dataset
uspto-grants-2002_01
Patent number
US06337341B1

Reaction notes

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