Hydrogen Peroxide → HCID 19006205, compound

HRID 1742926Notes

Reaction equation

HRID 1742926 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([O:10][CH2:11][CH:12]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[O:9])=[CH:4][N:3]=1.FC(F)(F)C(O)=[O:30].OO.C(Cl)(Cl)Cl>ClCCl.CC(OCC)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([O:10][CH2:11][CH:12]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[O:9])=[CH:4][N+:3]=1[O-:30]

Participants

7

Reactant 4

HCID 784Hydrogen Peroxide2×HCID 6212ChloroformHCID 6422Trifluoroacetic acidHCID 19006189HCID 19006189, compound

Product 1

HCID 19006205HCID 19006205, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product from Stage (a) (45.8 g, 0.12 mol) was dissolved in dichloromethane (350 ml) and trifluoroacetic acid (60 ml) was added dropwise during 30 minutes. H2O2 (100 vol, 31 ml, 0.24 mol) was then added during 15 minutes and the solution was boiled under reflux for 4 hours. A further addition of H2O2 (5 ml) was made and boiling was continued for a further 5 hours when it was shown by TLC (SiO2, CHCl3 :CH3CO2C2H5 =1:1) that only a trace of starting material remained. The mixture was poured onto ice and the organic solution was extracted with aqueous sodium carbonate and water, dried (MgSO4) and concentrated at 0.2 mm pressure to 46 g of oil. Microanalysis for C22H36NO3Cl, % theory (found): C: 66.39 (66.2); H: 9.12 (9.5); N: 3.52 (3.2); Cl: 8.91 (8.7). M.S. m/z=397. NMR(CDCl3)=7.65 (m, 2, ArH), 8.90 (2, 1, ArM), otherwise as starting material.

Workup

  1. temperatureunder reflux for 4 hours
  2. additionThe mixture was poured onto ice
  3. extractionthe organic solution was extracted with aqueous sodium carbonate and water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated at 0.2 mm pressure to 46 g of oil

Sources & evidence

ORD record
ord-fcfe055147e9423c971633588c153428
Source dataset
uspto-grants-1994_08
Patent number
US05342937

Reaction notes

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