Sodium Thiosulfate → HCID 23081388, compound

HRID 856130Notes

Reaction equation

HRID 856130 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]([CH3:27])[C:20](=[O:26])[O:21][CH2:22][C:23]([CH3:25])=[CH2:24])=[CH:15][CH:14]=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([N:19]([CH3:27])[C:20](=[O:26])[O:21][CH2:22][C:23]2([CH3:25])[CH2:24][O:9]2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 69480605HCID 69480605, compound

Product 1

HCID 23081388HCID 23081388, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

m-Chloroperbenzoic acid (2.5 g, 10.1 mmol) was added to a solution of 2-methyl-2-propenyl N-(4-chlorophenyl)-N-methylcarbamate (1.78 g, 6.7 mmol) in methylene chloride (20 ml) while cooling in an ice-bath, and the mixture was stirred at room temperature for 6.5 hours. To which sodium thiosulfate aqueous solution was added and the mixture was filtered, and sodium hydrogencarbonate aqueous solution was added to the filtrate. The organic layer was separated, dried over magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/methanol=20/1) to afford (2-methyl-2-oxiranylmethyl) N-(4-chlorophenyl)-N-methylcarbamate (1.7 g, quantitative) as a pale yellow oil.

Workup

  1. temperaturewhile cooling in an ice-bath
  2. filtrationthe mixture was filtered
  3. additionsodium hydrogencarbonate aqueous solution was added to the filtrate
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (methylene chloride/methanol=20/1)

Sources & evidence

ORD record
ord-2646d2665e9443ab89b6fb2dd3f76111
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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