Hydrogen Peroxide → HCID 23216865, compound

HRID 2247414Notes

Reaction equation

HRID 2247414 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:10]=1[CH2:16]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC(OP(OC2C=CC=CC=2)([N:27]=[N+]=[N-])=O)=CC=1.C1(C2CCCCCCCCC=2)CCCCCCCNN=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:76](OC([O-])=O)([O:78][C:79]([CH3:82])([CH3:81])[CH3:80])=[O:77].OO>C1(C)C=CC=CC=1.O1CCCC1.O.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:10]=1[CH2:16][NH:27][C:76](=[O:77])[O:78][C:79]([CH3:82])([CH3:81])[CH3:80])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

11

Reactant 6

HCID 784Hydrogen PeroxideHCID 11776TriphenylphosphineHCID 123414Diphenylphosphoryl azideHCID 897136(2-(Benzyloxy)-5-bromophenyl)methanolHCID 22064466Tert-butyldicarbonateHCID 66902059HCID 66902059, compound

Product 1

HCID 23216865HCID 23216865, compoundYield 69.9%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

[2-(Benzyloxy)-5-bromophenyl]methanol (140.3 g) was dissolved in 700 ml of toluene, 160 g of diphenyl phosphorazide and 85 g of diazabicyclodecene were successively added to the solution, and the mixture was stirred overnight at room temperature. 1 L of ethyl acetate was added thereto, and the reaction mixture was successively washed with water and brine, dried over anhydrous magnesium sulfate, and the solvent was removed to give 157 g of 1-[2-(benzyloxy)-5-bromobenzyl]-1,2-triazadien-2-ium. 47.23 g of the product was dissolved in 500 ml of tetrahydrofuran and 20 ml of water, 42 g of triphenyl phosphine was added thereto, and the mixture was stirred overnight. 28 g of t-butyl dicarbonate was added thereto and stirred at room temperature for 1 hour, and 3 ml of 30% aqueous hydrogen peroxide was added thereto. The solvent was concentrated and the residue was suspended in diethyl ether and filtered. The filtrate was evaporated, and the residue was purified by silica gel column, to give 47.645 g of the title compound in the 15:1→10:1 hexane-ethyl acetate fraction.

Workup

  1. washthe reaction mixture was successively washed with water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was removed
  4. customto give 157 g of 1-[2-(benzyloxy)-5-bromobenzyl]-1,2-triazadien-2-ium
  5. stirringthe mixture was stirred overnight
  6. stirringstirred at room temperature for 1 hour
  7. concentrationThe solvent was concentrated
  8. filtrationfiltered
  9. customThe filtrate was evaporated
  10. customthe residue was purified by silica gel column

Sources & evidence

ORD record
ord-98116499e8304b51bbf9dffcfb24d954
Source dataset
uspto-grants-2010_03
Patent number
US07687664B2

Reaction notes

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