Sodium Thiosulfate → HCID 86604798, compound

HRID 856125Notes

Reaction equation

HRID 856125 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([O:10]O)=O)[CH:3]=1.CC(=C)C[N:15]1[C:20]2C=CC=[CH:24][C:19]=2[CH2:18][O:17][C:16]1=[O:25].S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH3:24][C:19]1([CH2:20][N:15]2[C:5]3[CH:6]=[CH:7][CH:2]=[CH:3][C:4]=3[CH2:8][O:10][C:16]2=[O:25])[CH2:18][O:17]1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 69479748HCID 69479748, compound

Product 1

HCID 86604798HCID 86604798, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

m-Chloroperbenzoic acid (13.76 g, 55.81 mmol) was added to a solution of 1-(2-methyl-2-propenyl)-1,4-dihydrobenzo[d][1,3]oxazin-2-one (7.09 g, 34.88 mmol) in methylene chloride (150 ml), and the mixture was stirred at room temperature for 24 hours. To the mixture, sodium thiosulfate aqueous solution and sodium hydrogencarbonate aqueous solution were added, and the resulting mixture was filtered. The organic layer was separated, washed with sodium hydrogencarbonate aqueous solution, dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1) to afford 1-(2-methyl-2-oxiranylmethyl)-1,4-dihydrobenzo[d][1,3]oxazin-2-one (5.13 g, 67%) as a pale yellow oil.

Workup

  1. filtrationthe resulting mixture was filtered
  2. customThe organic layer was separated
  3. washwashed with sodium hydrogencarbonate aqueous solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-c5a5918c8b714ee8ae7cdfb23abbc420
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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