Dichloromethane → HCID 45080601, compound

HRID 1055628Notes

Reaction equation

HRID 1055628 reaction equation
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[S:8]([NH2:11])(=[O:10])=[O:9].C(=O)(O)[O-:13].[Na+].ClCCl.ClC1C=CC=C(C(OO)=O)C=1>O>[O:13]1[CH:6]2[CH:5]1[CH:4]1[CH2:7][CH:1]2[CH:2]([S:8]([NH2:11])(=[O:9])=[O:10])[CH2:3]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 22094258Bicyclo[2.2.1]hept-5-ene-2-sulfonamide

Product 1

HCID 45080601HCID 45080601, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

To a four-necked flask having an inner volume of 500 ml and equipped with an electromagnetic stirring device, a nitrogen inlet tube, and a thermometer, there were charged 10.0 g (57.7 mmol) of 5-norbornene-2-sulfonamide, 15.1 g (180.0 mmol) of sodium bicarbonate, and 200 g of dichloromethane. After cooling the mixture to 5° C., 14.8 g (60.0 mmol) of 70% m-chloroperbenzoic acid was added thereto over a 20 minute period, and the mixture was stirred at 5° C. for 2 hours. To the reaction mixture was added 100 g of distilled water, and the mixture was separated into an organic layer and an aqueous layer. The organic layer was washed with 40 g of distilled water and concentrated under reduced pressure. By recrystallizing the residue obtained from ethyl acetate, there was obtained 6.89 g (36.4 mmol) of 5,6-epoxy-2-norbornanesulfonamide represented by the following formula (yield 63%):

Workup

  1. customTo a four-necked flask having
  2. customan inner volume of 500 ml and equipped with an electromagnetic stirring device, a nitrogen inlet tube
  3. customthe mixture was separated into an organic layer
  4. washThe organic layer was washed with 40 g of distilled water
  5. concentrationconcentrated under reduced pressure
  6. customBy recrystallizing the residue
  7. customobtained from ethyl acetate

Sources & evidence

ORD record
ord-8269be94461546c8884137fefd17ec64
Source dataset
uspto-grants-2016_07
Patent number
US09395625B2

Reaction notes

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