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

HRID 2246479Notes

Reaction equation

HRID 2246479 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-4bb5d4ca0546466b82ba2295b2d3fc48
Source dataset
uspto-grants-2010_03
Patent number
US07687525B2

Reaction notes

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