m-Chloroperbenzoic acid → 3-(2-methyl-2-oxiranylmethyl)-3H-benzoxazol-2-one

HRID 856126Notes

Reaction equation

HRID 856126 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][C:13](=[CH2:25])[CH2:14][N:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[O:17][C:16]1=[O:24]>C(Cl)Cl>[CH3:25][C:13]1([CH2:14][N:15]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[O:17][C:16]2=[O:24])[CH2:12][O:9]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 230812413-(2-methyl-2-propenyl)-3H-benzoxazol-2-one

Product 1

HCID 230815373-(2-methyl-2-oxiranylmethyl)-3H-benzoxazol-2-oneYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

m-Chloroperbenzoic acid (1.66 g, 9.65 mmol) was added to a mixture of 3-(2-methyl-2-propenyl)-3H-benzoxazol-2-one (1.66 g, 8.77 mmol) in methylene chloride (30 ml) while cooling in an ice-bath, and the mixture was stirred at room temperature overnight. The reaction mixture was filtered, and the filtrate was washed with a 20% sodium sulfite aqueous solution, saturated sodium bicarbonate aqueous solution and brine, and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was treated with methylene chloride/n-hexane, and the resulting precipitates were collected by filtration to afford 3-(2-methyl-2-oxiranylmethyl)-3H-benzoxazol-2-one (1.78 g, yield 99%) as a white powder.

Workup

  1. temperaturewhile cooling in an ice-bath
  2. filtrationThe reaction mixture was filtered
  3. washthe filtrate was washed with a 20% sodium sulfite aqueous solution, saturated sodium bicarbonate aqueous solution and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. additionThe residue was treated with methylene chloride/n-hexane
  8. customthe resulting precipitates
  9. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-11e6e1350b064307a9548d1f0ac4d730
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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