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

HRID 2250449Notes

Reaction equation

HRID 2250449 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 1/2 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 to 1/2 volume by evaporation
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. customdried
  6. customevaporated
  7. customThe residue was purified by column chromatography (eluent: chloroform)
  8. customto give a solid, which
  9. washwas then washed with diethyl ether

Sources & evidence

ORD record
ord-4ebd81a874e14bf49a4bfece99d65ace
Source dataset
uspto-grants-2008_01
Patent number
US07317028B2

Reaction notes

Loading…