m-Chloroperbenzoic acid → HCID 13984051, compound

HRID 568939Notes

Reaction equation

HRID 568939 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:9])=[C:6]([O:17][CH2:18][CH2:19][CH3:20])[CH:5]=[C:4]([CH3:21])[N:3]=1.ClC1C=CC=C(C(OO)=[O:30])C=1.S([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[CH3:1][C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:9])=[C:6]([O:17][CH2:18][CH2:19][CH3:20])[CH:5]=[C:4]([CH3:21])[N+:3]=1[O-:30]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 13984001HCID 13984001, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 13984051HCID 13984051, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Then a mixture of 1.42 g (5 m mol) of 2,6-dimethyl-N-phenyl-4-propoxy-3-pyridinecarboxamide obtained thus, 2.16 g (10 m mol) of a commercially available m-chloroperbenzoic acid (80% purity) and 40 ml of chloroform was stirred for 8 hours at room temperature. The reaction mixture was discharged to a separation funnel and after the addition of the 10% aqueous sodium hydrogen sulfite solution, was shaken. The separated oil phase was washed with aqueous saturated sodium hydrogen carbonate solution and then with aqueous saturated sodium chloride solution. It was then dehydrated over anhydrous magnesium sulfate and filtered. After the filtrate was concentrated, the residue was crystallized from a mixture of ethyl acetate and hexane to obtain 1.37 g of the title compound

Workup

  1. customobtained thus
  2. customThe reaction mixture was discharged to a separation funnel
  3. washThe separated oil phase was washed with aqueous saturated sodium hydrogen carbonate solution
  4. filtrationfiltered
  5. concentrationAfter the filtrate was concentrated
  6. customthe residue was crystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-358c4dc905f446eba3f6afe053e375c0
Source dataset
uspto-grants-1988_03
Patent number
US04730051

Reaction notes

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