Sodium Thiosulfate → HCID 86604809, compound

HRID 856128Notes

Reaction equation

HRID 856128 reaction equation
[CH3:1][C:2](=[CH2:15])[CH2:3][NH:4][C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.ClC1C=CC=C(C(OO)=[O:24])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH2:7]([O:6][C:5](=[O:14])[NH:4][CH2:3][C:2]1([CH3:1])[CH2:15][O:24]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 13294368HCID 13294368, compound

Product 1

HCID 86604809HCID 86604809, compoundYield 102.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzyl N-(2-methyl-2-propenyl)carbamate (3.90 g, 19.0 mmol) prepared in Reference Example 173 was dissolved in methylene chloride (80 ml), to which m-chloroperbenzoic acid (5.15 g, 20.9 mmol) was added, and the mixture was stirred at room temperature overnight. Sodium thiosulfate aqueous solution and saturated sodium hydrogencarbonate aqueous solution were added to the reaction mixture, which was stirred for a while. The organic layer was separated, washed with saturated sodium hydrogencarbonate aqueous solution, dried over sodium sulfate, and then filtered. The filtrate was concentrated under reduced pressure to afford benzyl(2-methyl-2-oxiranylmethyl)carbamate (4.31 g, quantitative) as a colorless oil.

Workup

  1. additionwas added
  2. stirringwas stirred for a while
  3. customThe organic layer was separated
  4. washwashed with saturated sodium hydrogencarbonate aqueous solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-87be13e1adce404a9675165522a1459d
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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