m-Chloroperbenzoic acid → HCID 14555181, compound

HRID 1723193Notes

Reaction equation

HRID 1723193 reaction equation
[CH3:1][S:2][CH2:3][C:4]([NH:6][C:7]1[C:12]([CH3:13])=[CH:11][CH:10]=[CH:9][C:8]=1[CH3:14])=[O:5].ClC1C=CC=C(C(OO)=[O:23])C=1>C(Cl)Cl>[CH3:1][S:2]([CH2:3][C:4]([NH:6][C:7]1[C:12]([CH3:13])=[CH:11][CH:10]=[CH:9][C:8]=1[CH3:14])=[O:5])=[O:23]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 14555179HCID 14555179, compound

Product 1

HCID 14555181HCID 14555181, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

To a methylene chloride solution containing 2.09 g (10 mmol) of 2-methylthio-N-(2,6-dimethylphenyl)acetamide was added, in portions over 30 min with stirring at 5° C., 2.16 g (10 mmol) of m-chloroperbenzoic acid (80% solution). The reaction mixture was kept at 5° C. for an additional 1.25 hr. The precipitate formed was filtered and washed twice with methylene chloride. The filtrate and washings were combined, washed once with saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate, and evaporated under reduced pressure. The residue was recrystallized from ethyl acetate to afford white crystalline compound (88% yield), mp 112°-114° C.

Workup

  1. additionwas added, in portions over 30 min
  2. customThe precipitate formed
  3. filtrationwas filtered
  4. washwashed twice with methylene chloride
  5. washwashed once with saturated aqueous sodium bicarbonate solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-4f40bd7a99474219abf526aeb9edc0f9
Source dataset
uspto-grants-1989_08
Patent number
US04859707

Reaction notes

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