m-Chloroperbenzoic acid → HCID 53828394, compound

HRID 259251Notes

Reaction equation

HRID 259251 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11][CH2:12][CH2:13][CH2:14][CH3:15])=[CH:7][N:6]=1)=[O:4].ClC1C=CC=C(C(OO)=[O:24])C=1>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH2:12][CH2:13][CH2:14][CH3:15])=[O:24])=[CH:7][N:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 53943436HCID 53943436, compound

Product 1

HCID 53828394HCID 53828394, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To the stirred solution of 6.5 g of 5-n-butylmercapto-pyridine-2-carboxylic acid methyl ester in 200 ml of methylene chloride, the solution of 5.7 g of m-chloroperbenzoic acid in 100 ml of methylene chloride is added during 15 minutes while cooling with ice. It is stirred another 15 minutes and allowed to stand at room temperature overnight. It is washed with 10% aqueous sodium bicarbonate and water, dried and evaporated. The residue is recrystallized from benzene-hexane (1:1), to yield the 5-n-butylsulfinylpyridine-2-carboxylic acid methyl ester melting at 150°-154°.

Workup

  1. temperaturewhile cooling with ice
  2. waitto stand at room temperature overnight
  3. washIt is washed with 10% aqueous sodium bicarbonate and water
  4. customdried
  5. customevaporated
  6. customThe residue is recrystallized from benzene-hexane (1:1)

Sources & evidence

ORD record
ord-0538e09bc0534dd79dae737a47819ac4
Source dataset
uspto-grants-1977_07
Patent number
US04036965

Reaction notes

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