O-Phenylenediamine → N-(tert-Butoxycarbonyl)-1,2-phenylenediamine

HRID 912475Notes

Reaction equation

HRID 912475 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[OH-].[Na+].[C:11]([O:15][C:16](OC([O-])=O)=[O:17])([CH3:14])([CH3:13])[CH3:12]>O1CCOCC1>[C:11]([O:15][C:16]([NH:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[NH2:8])=[O:17])([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 7243O-PhenylenediamineHCID 14798Sodium HydroxideHCID 22064466Tert-butyldicarbonate

Product 1

HCID 676311N-(tert-Butoxycarbonyl)-1,2-phenylenediamineYield 32.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 108 g of o-phenylenediamine (1.0 mol) in 1000 mL of dioxane was added 500 mL of 1N sodium hydroxide aq., and then 218 g of tert-butyldicarbonate (1.1 mol) in 500 mL of dioxane under ice-cooling. After stirring for 6 hours at room temperature, the mixture was left overnight. The mixture was concentrated to ½ volume by evaporation, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried and evaporated. The residue was purified by column chromatography (eluent: chloroform) to give a solid, which was then washed with diethyl ether to give 68.4 g of N-tert-butoxycarbonyl-o-phenylenediamine (Yield: 32.8%) as a white solid.

Workup

  1. waitthe mixture was left overnight
  2. concentrationThe mixture was concentrated
  3. customby evaporation
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. customdried
  7. customevaporated
  8. customThe residue was purified by column chromatography (eluent: chloroform)
  9. customto give a solid, which
  10. washwas then washed with diethyl ether

Sources & evidence

ORD record
ord-eb6442feca3a4abf9c97d6ee2140fc81
Source dataset
uspto-grants-2011_09
Patent number
US08026239B2

Reaction notes

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